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Preparation of pyrazine deriva tives as checkpoint kinase 1 inhibitors useful in treatment of cancers

By: Pinkerton, Anthony B.; et al

World Intellectual Property Organization, WO2022251502 A1 2022-12-01

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A practical synthesis of voxelotor

By: Kang, Linlin; et al

Journal of Heterocyclic Chemistry (2022), 59(11), 1990-1995.

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31-614-CAS-33566137 Steps: 1 Yield: 65%

1.1 Reagents: Butyllithium

Solvents: Hexane; -25 - - 20 °C; 30 min, - 25 - - 20 °C

1.2 Solvents: Tetrahydrofuran; 30 min, - 25 - - 20 °C; 3 h, - 25 - - 20 °C

1.3 Reagents: Water

Process for preparation of tricyclic usp1 inhibitor and use thereof

By: Liu, Bin

World Intellectual Property Organization, WO2022228399 A1 2022-11-03

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Preparation of purine deriva tives for use as antitumor agents

By: Throner, Scott; et al

World Intellectual Property Organization, WO2022197892 A1 2022-09-22

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31-614-CAS-34497056 Steps: 1 Yield: 64%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -40 °C; - 40 °C → 0 °C; 1 h, 0 °C; 0 °C → - 78 °C

1.2 -78 °C → rt; 12 h, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; 0 °C

Preparation of C DK inhibitors and methods of use thereof

By: Taylor, Alexander M.; et al

World Intellectual Property Organization, WO2022174031 A1 2022-08-18

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Combination of intracellular and extrace llular photosen sitizers for treatment of bacterial infection

By: Skaar, Eric

World Intellectual Property Organization, WO2022165023 A1 2022-08-04

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31-614-CAS-33823907 Steps: 1 Yield: 70%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -60 °C; 5 min, - 60 °C

1.2 -60 °C → rt
1.3 Solvents: Water; rt

Class of morpholine derivatives, preparation method therefor and applic ation thereof

By: Wang, Wei; et al

World Intellectual Property Organization, WO2022152229 A1 2022-07-21

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Continuous Processing of Concen trated Organol ithiums in Flow Using Static and Dynamic Spinning Disc Reactor Techno logies

By: Wietelmann, Ulrich; et al

Organic Process Research & Development (2022), 26(5), 1422-1431.

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Suppliers (91) Suppliers (85) Suppliers (107)

31-614-CAS-32106560 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 5 °C; - 78 °C

Process preparation of GBT440, 2- hydroxy-6- ((2- (1-isopropyl- 1h-pyrazol-5- yl)pyridin-3- yl)methoxy)benzaldehyde

By: Wang, Fang; et al

World Intellectual Property Organization, WO2022099064 A2 2022-05-12

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31-614-CAS-32434283 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Heptane; rt → 15 °C

10

Preparation of azolecarb oxamides as PPARγ modulators and methods of use

By: Prajapati, Sudeep; et al

World Intellectual Property Organization, WO2022099144 A1 2022-05-12

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Supplier (1)

31-614-CAS-32526236 Steps: 1

1.1 Reagents: Bis(pinacolato)diborane

Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine
Solvents: tert-Butyl methyl ether; 14 h, 80 °C

11

Preparation of heterocyclic spiro compounds, especi ally, substituted 2- acryloyl-6- (5, 6,7,8- tetrahydroquinazolin-2- yl)- 2,6- diazaspiro
[3.4]octanes and related compounds as G12 C mutant K RAS protein inhibitors for treating cancers

By: Lanman, Brian Alan; et al

World Intellectual Property Organization, WO2022083569 A1 2022-04-28

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31-614-CAS-32325256 Steps: 1

1.1 Reagents: Potassium fluoride

Solvents: Acetonitrile; 2 h, rt

12

Central control method for synthesis reaction of 1- isopropyl pyrazole-5- boronic acid pinacol ester by gas chromat ography

By: Lu, Qian; et al

China, CN114213437 A 2022-03-22

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31-614-CAS-31972843 Steps: 1
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1.1 Reagents: Butyllithium

Solvents: Dichloromethane

13

Synthesis method of 1- isopropyl pyrazole-5- boronic acid pinacol ester as interm ediate of voxelotor for treating sickle cell disease

By: Lu, Qian; et al

China, CN114181237 A 2022-03-15

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31-614-CAS-31928123 Steps: 1 Yield: 77%

1.1 Reagents: Ammonia

Solvents: Tetrahydrofuran; -60 °C; - 60 °C → - 45 °C; 2 h, - 45 °C

1.2 -45 °C; - 35 °C

1.3 Reagents: Ammonium chloride
Solvents: Water

14

Preparation of heteroaromatic compounds as A TR inhibitors and uses thereof

By: Shan, Bo; et al

World Intellectual Property Organization, WO2022028598 A1 2022-02-10

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31-614-CAS-31602032 Steps: 1 Yield: 34%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C; 30 min, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C; 1 h, - 78 °C

1.3 Reagents: Hydrochloric acid
Solvents: Water; 0.5 h, rt

15

Preparation of fused bicyclic Raf inhibitors and methods for use thereof
 SciFinderⁿ® Page 8

By: Belfield, Andrew; et al

World Intellectual Property Organization, WO2022023447 A2 2022-02-03

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31-614-CAS-31545566 Steps: 1 Yield: 100%

1.1 Reagents: Potassium acetate

Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct
Solvents: 1,4-Dioxane; 1 h, rt → 85 °C

16

Merging Halogen- Atom Transfer (X AT) and Copper Catalysis for the Modular Suzuki- Miyaura- Type Cross-Coupling of Alkyl Iodides
and Organo borons

By: Zhang, Zhenhua; et al

Journal of the American Chemical Society (2022), 144(4), 1986-1992.

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31-614-CAS-31059291 Steps: 1

1.1 Solvents: Tetrahydrofuran, Hexane; -78 °C; 1 min, - 78 °C; - 78 °C → rt; 1 h, rt

Experimental Protocols

17

Preparation of indole compounds as androgen receptor modulators

By: Bakary-Barry, Toure; et al

World Intellectual Property Organization, WO2022020342 A1 2022-01-27

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31-614-CAS-31476618 Steps: 1 Yield: 53%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 0.5 h, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C; 2 h, - 78 °C

1.3 Reagents: Ammonium chloride
Solvents: Water; -78 °C
1.4 Reagents: Hydrochloric acid
Solvents: Water; pH 5

18

Preparation of pyrrolopyridinone derivatives for use as bromod omain and extraterminal inhibitors

By: Fang, Haiquan; et al

World Intellectual Property Organization, WO2022012456 A1 2022-01-20

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31-614-CAS-31455437 Steps: 1 Yield: 49%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Heptane; rt → 70 °C; overnight, 70 °C

19

Cd73 inhibitor and applic ation in pharmaceutical use

By: Wu, Hao; et al

World Intellectual Property Organization, WO2022007677 A1 2022-01-13

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31-614-CAS-31342372 Steps: 1

1.1 Reagents: Potassium carbonate

Solvents: Acetonitrile; overnight, rt → 70 °C

20

Preparation of macrocycles and their use as anticancer agents

By: Cui, Jingrong Jean

World Intellectual Property Organization, WO2022011123 A1 2022-01-13

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31-614-CAS-31350929 Steps: 1 Yield: 22%

1.1 Reagents: Lithium diisopropylamide

Solvents: 2-Methyltetrahydrofuran; 0.5 h, 25 °C

1.2 Reagents: Triisopropyl borate

Solvents: 2-Methyltetrahydrofuran; 1.5 h, 25 °C
1.3 Reagents: Methanol

21

Azolylalk anamides as small molecule modulators of I L-17 and their prepar ation

By: Andrews, Mark; et al

World Intellectual Property Organization, WO2021255174 A1 2021-12-23

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31-614-CAS-31091580 Steps: 1 Yield: 17%

 SciFinderⁿ® Page 11

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -75 °C; 30 min, - 75 °C

1.2 -78 °C → rt; 1 h, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; rt

22

N-Linked macrocyclic 4- (pyrazol-5- yl)- indole deriva tives as inhibitors of M CL-1 and their prepar ation

By: Peschiulli, Aldo; et al

World Intellectual Property Organization, WO2021255258 A1 2021-12-23

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31-614-CAS-31072492 Steps: 1 Yield: 74%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 45 min, - 78 °C

1.2 -78 °C; - 78 °C → rt; 16 h, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; rt

23

N-Linked macrocyclic 7- (pyrazol-5- yl)- indole deriva tives as inhibitors of M CL-1 and their prepar ation

By: Rombouts, Frederik Jan Rita; et al

World Intellectual Property Organization, WO2021255257 A1 2021-12-23

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31-614-CAS-31147288 Steps: 1 Yield: 74%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 45 min, - 78 °C

1.2 -78 °C → rt; 16 h, rt

1.3 Reagents: Ammonium chloride
Solvents: Water

24
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Nitrogen-containing fused bicyclic compounds and their use as ubiquitin- specific-processing protease 1 (U SP1) inhibitors

By: Brenneman, Jehrod Burnett; et al

World Intellectual Property Organization, WO2021247606 A1 2021-12-09

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31-614-CAS-27647041 Steps: 1

1.1 Reagents: Cesium carbonate

Solvents: Acetonitrile; 2 h, 80 °C; 80 °C → rt

1.2 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 0 °C; 1 h, rt; rt → - 78 °C
1.3 -78 °C; - 78 °C → rt; 2 h, rt
1.4 Reagents: Ammonium chloride
Solvents: Water; rt

25

Preparation of heterocyclic compounds as S TIN G modulators

By: Li, Jing; et al

World Intellectual Property Organization, WO2021239068 A1 2021-12-02

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31-614-CAS-25247999 Steps: 1 Yield: 14%

1.1 Reagents: Butyllithium, 1-Ethyl-5-methyl-1H-pyrazole

Solvents: Tetrahydrofuran; -78 °C; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; 1 h, - 78 °C; - 78 °C → rt

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26

Macrocyclic 7- pyrazol-5- yl-indole deriva tives as Mcl-1 inhibitors

By: Rombouts, Frederik Jan Rita; et al

World Intellectual Property Organization, WO2021239862 A1 2021-12-02

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31-614-CAS-30633823 Steps: 1 Yield: 100%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 1 h, - 78 °C

1.2 -78 °C; - 78 °C → rt; 2 h, rt

1.3 Reagents: Ammonium chloride
Solvents: Water

27

Preparation of piperazine cyclic ureas as inhibitors of cellular necrosis and/or human receptor intera cting protein 1 kinase (R IP1)

By: Su, Yaning; et al

World Intellectual Property Organization, WO2021233397 A1 2021-11-25

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31-614-CAS-25871779 Steps: 1 Yield: 90%

1.1 Reagents: Chlorosuccinimide

Solvents: Dimethylformamide; 8 h, 50 °C

28

Preparation of heteroaromatic macrocyclic ether chemothe rapeutic agents for treatment of cancer

By: Horan, Joshua Courtney; et al

World Intellectual Property Organization, WO2021226269 A1 2021-11-11

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Absolute stereochemistry shown Absolute stereochemistry shown

31-614-CAS-25097410 Steps: 1 Yield: 86%

1.1 Reagents: Lithium diisopropylamide

Solvents: Tetrahydrofuran; 5 min, - 78 °C; 1 h, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C; overnight, - 78 °C → rt

1.3 Reagents: Trifluoroacetic acid
Solvents: Dichloromethane; 1 h, rt

29

Preparation of heteroaromatic macrocyclic ether chemothe rapeutic agents for treatment of cancer

By: Tang, Xinxing; et al

World Intellectual Property Organization, WO2021226208 A2 2021-11-11

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31-614-CAS-25095946 Steps: 1 Yield: 57%

1.1 Reagents: Lithium diisopropylamide

Solvents: Tetrahydrofuran; -78 °C; 0.5 h, - 78 °C

1.2 Reagents: Trimethyl borate

Solvents: Tetrahydrofuran; -78 °C; 1 h, - 78 °C
1.3 Reagents: Ammonium chloride
Solvents: Water

30

Preparation of antibac terial 8- phenylamino-3- (pyrazol-4- yl)imidazo[1,2- a]pyrazine derivatives

By: Blanc, Jean-Baptiste; et al

World Intellectual Property Organization, WO2021219578 A1 2021-11-04

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Supplier (1) Suppliers (91) Supplier (1)

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31-614-CAS-24873014 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C; 40 min, - 78 °C

1.2 -78 °C

31

Heteroaryl- Heteroaryl Suzuki- Miyaura Anhydrous Cross- Coupling Reactions Enabled by Trimethyl Borate

By: Kassel, Vincent M.; et al

Journal of the American Chemical Society (2021), 143(34), 13845-13853.

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31-614-CAS-23956318 Steps: 1 Yield: 86%

1.1 Solvents: Tetrahydrofuran; 4 h, rt

Experimental Protocols

32

Fluorinated quinoline and quinox aline derivatives as dihydroorotate dehydro genase (DHODH) inhibitors for the treatment of cancer,
autoimmune and inflam matory diseases

By: Cisar, Justin; et al

World Intellectual Property Organization, WO2021084500 A1 2021-05-06

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Suppliers (128) Suppliers (23) Suppliers (4)

31-142-CAS-23653147 Steps: 1 Yield: 54%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Hexane; 15 min, rt

1.2 16 h, rt

33

Preparation of pyridaz inamine derivatives as modulators of S M ARCA2 and B RM target proteins and associated methods of use

By: Crew, Andrew P.; et al

World Intellectual Property Organization, WO2021067606 A1 2021-04-08

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31-614-CAS-33690590 Steps: 1 Yield: 45%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 0 °C; 1 h, rt; rt → - 78 °C

1.2 0.5 h, - 78 °C; - 78 °C → 0 °C

1.3 Reagents: Sodium chloride
Solvents: Water

34

Preparation of 3,4- dihydroqu inazolin-2- ylacetamides as human immunode ficiency virus replic ation inhibitors

By: Bowsher, Michael S.; et al

World Intellectual Property Organization, WO2021064677 A1 2021-04-08

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31-031-CAS-23858326 Steps: 1

1.1 Reagents: Cesium carbonate

Solvents: Acetonitrile; 2 h, 70 °C

35

Efficient preparation of aryl halides

By: Jiao, Ning; et al

China, CN112573978 A 2021-03-30

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31-084-CAS-24171420 Steps: 1 Yield: 96%

1.1 Reagents: Chlorosuccinimide

Catalysts: Piperidinium, 2,2,6,6-tetramethyl-, 1-oxide 1,1,1-trifluoromethanesulfonate (1:1)
Solvents: Chloroform; 12 h, 25 °C

36

Preparation of heterocyclic W DR5 inhibitors as anticancer agents

By: Fang, Lichao; et al

World Intellectual Property Organization, WO2021028806 A1 2021-02-18

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Suppliers (10) Suppliers (128) Suppliers (4)

31-614-CAS-28054797 Steps: 1 Yield: 81%

1.1 Reagents: Potassium acetate

Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium
Solvents: 1,4-Dioxane; 2 h, 80 °C

37

Preparation of heterocyclic W DR5 inhibitors as anticancer agents

By: Fang, Lichao; et al

World Intellectual Property Organization, WO2021026672 A1 2021-02-18

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31-614-CAS-24165743 Steps: 1 Yield: 81%

1.1 Reagents: Potassium acetate

Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct
Solvents: 1,4-Dioxane; 2 h, 80 °C

38

Compounds and methods for the targeted degrad ation of interleukin-1 receptor-associated kinase 1 proteins

By: Fu, Liqiang; et al

World Intellectual Property Organization, WO2021018118 A1 2021-02-04

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31-614-CAS-31298397 Steps: 1
 SciFinderⁿ® Page 19

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C; 5 min, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C → rt; 1 h, rt

1.3 Reagents: Acetic acid; 1 h, rt

39

Preparation of 1H-1,2,3- triazole-5- carboxylic acid deriva tives as glycolate oxidase inhibitors for the treatment of hyperox aluria and
related diseases

By: Wang, Bing; et al

World Intellectual Property Organization, WO2020257487 A1 2020-12-24

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31-142-CAS-23660879 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 30 min, - 78 °C

1.2 -78 °C → rt; 2 h, rt

40

A Mild Method for Making M IDA Boronates

By: Kelly, Aidan M.; et al

Organic Letters (2020), 22(24), 9408-9414.

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31-614-CAS-26691281 Steps: 1 Yield: 68%

1.1 Solvents: 1,4-Dioxane; 24 h, 70 °C

Experimental Protocols

41

Discovery of Novel and Highly Selective Cyclop ropane A LK Inhibitors through a Fragment- Assisted, Structure-Based Drug Design

By: Fujimori, Ikuo; et al

ACS Omega (2020), 5(49), 31984-32001.

 SciFinderⁿ® Page 20

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31-614-CAS-24860687 Steps: 1 Yield: 67%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C; 2 h, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C; - 78 °C → rt; 2 h, rt

1.3 Reagents: Acetic acid; overnight, rt
Experimental Protocols

42

Imidazo[1,2- c]pyrimidine derivatives as PRC2 inhibitors for treating cancer and their prepar ation

By: Marx, Matthew Arnord; et al

World Intellectual Property Organization, WO2020247475 A1 2020-12-10

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31-142-CAS-23073021 Steps: 1 Yield: 32%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Pentane; 20 min, 25 °C

1.2 Solvents: Pentane, Tetrahydrofuran; 24 h, 25 °C

43

1- Phenyl- 5- azinyl pyrazolyl- 3- oxyalkyl acids and their use for contro lling undesired plant growth

By: Hoffmann, Michael Gerhard; et al

World Intellectual Property Organization, WO2020245044 A1 2020-12-10

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31-614-CAS-31289282 Steps: 1 Yield: 59%

1.1 Reagents: Triethylamine

Catalysts: Bis(tri-tert-butylphosphine)palladium
Solvents: 1,4-Dioxane; 24 h, reflux

44

Practical Synthetic Method for Functio nalized 1- Methyl-3/5-(trifluoromethyl) - 1H-pyrazoles

By: Tairov, Maxim A.; et al

Organic Process Research & Development (2020), 24(11), 2619-2632.

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31-142-CAS-22818114 Steps: 1 Yield: 57%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 12 min, - 50 °C

1.2 Solvents: Tetrahydrofuran; 5 min, - 50 °C; 10 h, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; rt

45

Naphthyridine derivatives as PRC2 inhibitors and their prepar ation

By: Ketcham, John Michael; et al

World Intellectual Property Organization, WO2020219448 A1 2020-10-29

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 SciFinderⁿ® Page 22

31-142-CAS-22993240 Steps: 1 Yield: 32%

1.1 Reagents: 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium
Solvents: Pentane; 20 min, 25 °C

1.2 Solvents: Pentane, Tetrahydrofuran; 24 h, 25 °C

46

Tricyclic compounds as degraders of Ikaros and Aiolos and their prepar ation

By: Henderson, James A.; et al

World Intellectual Property Organization, WO2020210630 A1 2020-10-15

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31-113-CAS-23374112 Steps: 1 Yield: 62%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C; 1 h, - 78 °C; 30 min, - 78 °C

1.2 Reagents: Trimethyl borate; 2 h, - 78 °C; 1 h, - 78 °C

1.3 Reagents: Ammonium chloride
Solvents: Water

47

Formyl M IDA Boronate: C1 Building Block Enables Straight forward Access to α- Functionalized Organoboron Deriva tives

By: Ivon, Yevhen M.; et al

Angewandte Chemie, International Edition (2020), 59(41), 18016-18022.

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31-310-CAS-22675989 Steps: 1 Yield: 88%

1.1 Reagents: Acetic acid, Hydrazine hydrate (1:1)

Solvents: Dimethyl sulfoxide; 2 h, 30 °C

1.2 Reagents: Sodium chloride

Solvents: Water; 30 °C
Experimental Protocols

48

Macrocyclic azolopyridine derivatives as E ED and PRC2 modulators and their prepar ation

By: Efremov, Ivan Viktorovich; et al

World Intellectual Property Organization, WO2020190754 A1 2020-09-24

 SciFinderⁿ® Page 23

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31-614-CAS-31285745 Steps: 1 Yield: 56%

1.1 Reagents: Potassium acetate

Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium
Solvents: 1,4-Dioxane

49

Diethanolamine Boronic Esters: Develo pment of a Simple and Standard Process for Boronic Ester Synthesis

By: Inglesby, Phillip A.; et al

Organic Process Research & Development (2020), 24(9), 1683-1689.

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31-142-CAS-22541530 Steps: 1 Yield: 90%

1.1 Solvents: Isopropanol, 2-Methyltetrahydrofuran; 1 - 5 min, rt; 12 h, rt

Experimental Protocols

50

Acylamino bridged heterocyclic compound, and compos ition and applic ation thereof

By: Zhang, Qiang; et al

World Intellectual Property Organization, WO2020151589 A1 2020-07-30

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31-614-CAS-27626611 Steps: 1
 SciFinderⁿ® Page 24

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C; 1 h, - 78 °C

1.2 Reagents: Trimethyl borate; overnight, heated

1.3 Reagents: Ammonium chloride
Solvents: Water

51

Preparation of substituted pyrazolopy rimidines and substi tuted purines and their use as ubiquitin- specific-processing protease 1 (U
SP1) inhibitors

By: Brenneman, Jehrod Burnett; et al

World Intellectual Property Organization, WO2020132269 A1 2020-06-25

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31-614-CAS-29243043 Steps: 1

1.1 Reagents: Sodium hydride

Solvents: Tetrahydrofuran; 5 min, 0 °C; 30 min, 0 °C; 0 °C → rt

1.2 Solvents: Tetrahydrofuran; overnight, rt → reflux

1.3 Reagents: Water
1.4 Reagents: Butyllithium
Solvents: Tetrahydrofuran; 10 min, 0 °C; 1 h, 0 °C; 0 °C → - 78 °C
1.5 Solvents: Tetrahydrofuran; 5 min, - 78 °C; 30 min, - 78 °C; - 78 °C → rt; 4 h, rt
1.6 Reagents: Water

52

Pyrazole derivatives as H4 antagonists and their prepar ation

By: Brown, Giles; et al

World Intellectual Property Organization, WO2020079457 A1 2020-04-23

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Suppliers (91)

31-614-CAS-27186568 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate

Solvents: Tetrahydrofuran; 1 h, - 78 °C; overnight, - 78 °C → rt
1.3 Reagents: Acetic acid; 10 min, rt; 10 min, rt

53

Iridium-Catalyzed Silylation of Five- Membered Heteroa renes: High Sterically Derived Select ivity from a Pyridyl- Imidazoline Ligand

By: Karmel, Caleb; et al

Angewandte Chemie, International Edition (2020), 59(15), 6074-6081.

Suppliers (128) Suppliers (85) Suppliers (74)

31-142-CAS-21782342 Steps: 1 Yield: 37%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Tetrahydrofuran; 15 - 30 min, rt

1.2 rt; 15 h, 100 °C

Experimental Protocols

54

Two Distinct Mechanisms of Inhibition of Lpx A Acyltran sferase Essential for Lipopolys accharide Biosynthesis

By: Han, Wooseok; et al

Journal of the American Chemical Society (2020), 142(9), 4445-4455.

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 SciFinderⁿ® Page 26

Absolute stereochemistry shown Absolute stereochemistry shown

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Absolute stereochemistry shown Absolute stereochemistry shown

31-614-CAS-25573465 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Toluene, Tetrahydrofuran, Hexane; 1.5 h, - 78 °C; 2 h, - 78 °C; - 78 °C → rt; 1 h, rt

1.2 Reagents: Ammonium chloride

Solvents: Water; rt
Experimental Protocols

55

DM SO-catalysed late- stage chlorination of (hetero) arenes

By: Song, Song; et al

Nature Catalysis (2020), 3(2), 107-115.

Suppliers (107) Suppliers (30)

31-084-CAS-21557634 Steps: 1 Yield: 78%

1.1 Reagents: Chlorosuccinimide

Catalysts: Dimethyl sulfoxide
Solvents: Chloroform; 12 h, 25 °C

Experimental Protocols

56

Preparation of pyridaz inamine derivatives as modulators of S M ARCA2 and B RM target proteins and associated methods of use

By: Crew, Andrew P.; et al

United States, US20200038378 A1 2020-02-06

available
 SciFinderⁿ® Page 27

Suppliers (64) Suppliers (91) Suppliers (70)

31-142-CAS-22724391 Steps: 1 Yield: 45%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 0 °C; 1 h, rt; rt → - 78 °C

1.2 0.5 h, - 78 °C; - 78 °C → 0 °C

1.3 Reagents: Sodium chloride
Solvents: Water

57

Preparation of fused ring compound having urea structure as N AM PT inhibitor

By: Nakamura, Tsuyoshi; et al

World Intellectual Property Organization, WO2020010252 A1 2020-01-09

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58

Preparation of tricyclic compounds as bromod omain and B ET inhibitors

By: Fang, Haiquan; et al

World Intellectual Property Organization, WO2020001152 A1 2020-01-02

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31-614-CAS-26857885 Steps: 1 Yield: 99%

 SciFinderⁿ® Page 28

1.1 Reagents: Pinacolborane

Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine
Solvents: Tetrahydrofuran; rt → 55 °C; 1 h, 55 °C

1.2 Reagents: Water

59

A mild and simple method for making M IDA boronates

By: Kelly, Aidan M.; et al

ChemRxiv (2020), 1-6.

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31-614-CAS-28869310 Steps: 1 Yield: 68%

1.1 Solvents: 1,4-Dioxane; 24 h, 70 °C

Experimental Protocols

60

Preparation of aminopyridinyl pyrazoleca rboxamides as modulators of R ORγt for treatment of R ORγt-mediated diseases

By: Goldberg, Steven; et al

United States, US20190382373 A1 2019-12-19

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Suppliers (72) Suppliers (32) Supplier (1)

31-142-CAS-22553290 Steps: 1

1.1 Catalysts: 1,10-Phenanthroline, Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium

Solvents: Pentane; 20 min, 10 °C

1.2 Solvents: Pentane, Tetrahydrofuran; 16 h, rt

61

Preparation of pyridinyl pyrazoleca rboxamides as modulators of R ORgt for the treatment of R OR-γ-t-mediated diseases

By: Goldberg, Steven; et al

United States, US20190382350 A1 2019-12-19

 SciFinderⁿ® Page 29

available View 3 Related Reactions

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31-031-CAS-22553498 Steps: 1

1.1 Reagents: Potassium carbonate

Solvents: Tetrahydrofuran; rt; 24 h, reflux

1.2 Catalysts: 1,10-Phenanthroline, Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium

Solvents: Pentane; 20 min, 10 °C
1.3 Solvents: Pentane, Tetrahydrofuran; 16 h, rt

62

Discovery and biological evaluation of darolu tamide derivatives as inhibitors and down- regulators of wild- type AR and the mutants

By: Yu, Jiang; et al

European Journal of Medicinal Chemistry (2019), 182, 111608.

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63

Preparation of bifunc tional PROTAC compounds and methods for degrad ation of targeted BRM proteins

By: Crew, Andrew P.; et al

United States, US20190300521 A1 2019-10-03

available
 SciFinderⁿ® Page 30

Suppliers (64) Suppliers (91) Suppliers (70)

31-142-CAS-21876187 Steps: 1 Yield: 45%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 0 °C; 1 h, rt; rt → - 78 °C

1.2 0.5 h, - 78 °C; - 78 °C → 0 °C

1.3 Reagents: Sodium chloride
Solvents: Water

64

C-H Borylation Catalysts that Distinguish Between Similarly Sized Substi tuents Like Fluorine and Hydrogen

By: Miller, Susanne L.; et al

Organic Letters (2019), 21(16), 6388-6392.

Suppliers (72) Suppliers (85) Suppliers (107)

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31-142-CAS-20455421 Steps: 1 Yield: 60%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, [2,2′-Bipyridine]-4,4′-diamine, N 4,N 4,N 4′,N 4′-tetramethyl-

Solvents: Hexane; rt

1.2 Solvents: Hexane; 5 h, rt

65

Preparation of the A TR inhibitor and their medical applic ation

By: Qian, Wenyuan; et al

World Intellectual Property Organization, WO2019154365 A1 2019-08-15

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 SciFinderⁿ® Page 31

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31-142-CAS-22879563 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, 25 °C; 25 °C → - 78 °C

1.2 0.5 h, 78 °C; 78 °C → 0 °C; 1 h, 0 °C

1.3 Reagents: Sodium chloride
Solvents: Water; 0 - 5 °C
1.4 Reagents: Hydrochloric acid
Solvents: Water; pH 6 - 7

66

Preparation of dihydrobenzofuranylmethylaminoimidazopyrimidine derivatives for use as P RC2 inhibitors

By: Marx, Matthew Arnold; et al

World Intellectual Property Organization, WO2019152419 A1 2019-08-08

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Suppliers (72) Suppliers (65) Suppliers (21)

31-142-CAS-21493931 Steps: 1 Yield: 32%

1.1 Reagents: 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium
Solvents: Pentane; 20 min, 25 °C

1.2 Solvents: Pentane, Tetrahydrofuran; 24 h, 25 °C

67

Triazolecarboxylic acid deriva tives as glycolate oxidase inhibitors for the treatment of disease and their prepar ation

By: Wang, Bing; et al

World Intellectual Property Organization, WO2019133770 A2 2019-07-04

available View 7 Related Reactions

 SciFinderⁿ® Page 32

Suppliers (91)

31-142-CAS-21567100 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 30 min, - 78 °C

1.2 -78 °C → rt; 2 h, rt

68

Salt serving as akt inhibitor and crystal thereof

By: Li, Gang; et al

World Intellectual Property Organization, WO2019114741 A1 2019-06-20

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31-142-CAS-20591333 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -40 - - 20 °C; 1 h, - 40 - - 20 °C

1.2 -40 - - 20 °C; 40 min

1.3 Reagents: Ammonium chloride
Solvents: Water
1.4 Reagents: Hydrochloric acid
Solvents: Water; pH 5 - 6

69

Organol ithium process under continuous flow conditions

By: Schnippering, Stefan; et al

World Intellectual Property Organization, WO2019096762 A1 2019-05-23

available
 SciFinderⁿ® Page 33

Suppliers (85) Suppliers (91) Suppliers (107)

31-142-CAS-20642601 Steps: 1 Yield: 66%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; rt

1.2 Solvents: Tetrahydrofuran; 5 min, rt

1.3 -

70

Discovery of potent, selective, and brain- penetrant 1 H-pyrazol-5- yl-1H-pyrrolo[2,3- b]pyridines as anaplastic lymphoma kinase (A LK)
inhibitors

By: Fushimi, Makoto; et al

Journal of Medicinal Chemistry (2019), 62(10), 4915-4935.

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31-614-CAS-25732749 Steps: 1 Yield: 67%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C; 2 h, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C → rt; 2 h, rt

1.3 Reagents: Acetic acid; overnight, rt

71

Preparation of imidazo[1,2- a]pyrazines and related compounds as P I3K-γ inhibitors useful for treatment of cancer, autoim mune,
cardiovascular, and neurodege nerative diseases

By: Douty, Brent; et al

World Intellectual Property Organization, WO2019079469 A1 2019-04-25

available
 SciFinderⁿ® Page 34

Suppliers (90) Suppliers (37) Suppliers (91)

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31-031-CAS-20928760 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 2 min, 0 °C

1.2 0 °C → 30 °C; 23 h, 20 - 30 °C; 30 °C → 0 °C

1.3 Reagents: Butyllithium
Solvents: Hexane; 1 h, 0 °C → 30 °C; 30 °C → - 78 °C
1.4 15 min, - 78 °C; - 78 °C → 30 °C; overnight, 20 - 30 °C

72

Pharmaceutical agent containing azole- substituted pyridine compounds for inhibition of 20- HETE-producing enzyme

By: Tanaka, Hiroaki; et al

Japan, JP2019034932 A 2019-03-07

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73

Preparation of pyridine compounds substi tuted with azoles

By: Tanaka, Hiroaki; et al

World Intellectual Property Organization, WO2019031618 A1 2019-02-14

available
 SciFinderⁿ® Page 35

Product Only Reaction

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74

Preparation of pyrazole, isothi azole and isoxazole deriva tives useful as agricu ltural fungicides

By: Urch, Christopher John; et al

World Intellectual Property Organization, WO2019020981 A1 2019-01-31

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31-614-CAS-31227412 Steps: 1 Yield: 57%

1.1 Reagents: Potassium acetate

Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium
Solvents: Dimethylformamide; 2 h, rt → 130 °C

75

Iridium-catalyzed silylation of five- membered heteroarenes: high sterically derived selectivity from a pyridyl- imidazoline ligand

By: Karmel, Caleb; et al

ChemRxiv (2019), 1-10.

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31-142-CAS-20943759 Steps: 1 Yield: 37%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Tetrahydrofuran; 15 - 30 min, rt

1.2 15 h, 100 °C
Experimental Protocols
 SciFinderⁿ® Page 36

76

5- 5 Fused ring as C5a inhibitors and their prepar ation

By: Fan, Pingchen; et al

World Intellectual Property Organization, WO2018222601 A1 2018-12-06

available View 10 Related Reactions

31-142-CAS-20930284 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 1 h, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C → rt; 16 h, rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; rt

77

6- 5 Fused ring as C5a inhibitors and their prepar ation

By: Fan, Pingchen; et al

World Intellectual Property Organization, WO2018222598 A1 2018-12-06

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31-614-CAS-25298212 Steps: 1

1.1 Reagents: Potassium carbonate

Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct
Solvents: 1,4-Dioxane, Water; 7 h, 100 °C

78

Cobalt- Catalyzed C-H Borylation of Alkyl Arenes and Hetero arenes Including the First Selective Boryla tions of Secondary Benzylic C- H
Bonds

By: Jayasundara, Chathurika R. K.; et al

Organometallics (2018), 37(10), 1567-1574.

 SciFinderⁿ® Page 37

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31-142-CAS-19105698 Steps: 1 Yield: 90%

1.1 Catalysts: (T-4)-Bis[1,3-dihydro-1,3-bis(1-methylethyl)-2H-imidazol-2-ylidene]bis(2-methyl-2-propanolato)cobalt; 5 min, rt

1.2 48 h, 80 °C
Experimental Protocols

79

Preparation of O-lactam substi tuted phenyl ethers as hemoglobin modulators

By: Metcalf, Brian W.; et al

United States, US9981939 B2 2018-05-29

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31-142-CAS-20453755 Steps: 1 Yield: 47%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -30 °C; 30 min, - 30 °C

1.2 -78 °C; 3 h, - 78 °C

1.3 Reagents: Water

80

A Practical Telescoped Three- Step Sequence for the Prepar ation of (1R,2R)- 2- (4-Bromobenzoyl)cyclohexanecarboxylic Acid: A Key
Building Block Used in One of Our Drug Development Projects

By: Karlsson, Staffan; et al

Organic Process Research & Development (2018), 22(5), 618-624.

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 SciFinderⁿ® Page 38

31-614-CAS-29029234 Steps: 1 Yield: 84%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 30 min, - 50 °C

1.2 Reagents: Triisopropyl borate; 25 min, - 40 °C; - 40 °C → 20 °C

1.3 Reagents: Acetic acid; 17 h, 20 °C

81

Crystalline form of (1 R,2R)- 2- [4-(3-methy1-1H-pyrazol-5- yl)benzoyl]- n-(4-oxo-4,5,6,7- tetrahydropyrazolo [1,5- α]pyrazin-3- yl)cyclohex
anecarboxamide

By: Petersen, Matilda Angelica

World Intellectual Property Organization, WO2018078097 A1 2018-05-03

available

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82

Methods for forming saturated (hetero) cyclic borylated hydrocarbons and related compounds

By: Smith, Milton R., III; et al

United States, US20180051042 A1 2018-02-22

available

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31-031-CAS-22089122 Steps: 1

No Data Available

83

Preparation of inhibitors of cyclin dependent kinase 7 (C DK7)

By: Marineau, Jason J.; et al

World Intellectual Property Organization, WO2018013867 A1 2018-01-18

available
 SciFinderⁿ® Page 39

Suppliers (132) Suppliers (93) Suppliers (53)

31-031-CAS-21397535 Steps: 1

1.1 Reagents: Sodium hydride

Solvents: Tetrahydrofuran; 0 °C; 30 min, 15 °C; 15 °C → 0 °C

1.2 12 h, 15 °C
1.3 Reagents: Water

84

Hydroxyquinolinone compounds as muscarinic receptor antago nists and beta2 adrenergic receptor agonists and their prepar ation

By: Rancati, Fabio; et al

World Intellectual Property Organization, WO2018011090 A1 2018-01-18

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31-142-CAS-22089029 Steps: 1

1.1 Reagents: Potassium carbonate

Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct
Solvents: 1,4-Dioxane; 3 h, 80 °C

85

Decarbox ylative Benzyl ation of Aryl and Alkenyl Boronic Esters

By: Moon, Patrick J.; et al

Angewandte Chemie, International Edition (2018), 57(17), 4612-4616.

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31-614-CAS-30667805 Steps: 1

No Data Available
 SciFinderⁿ® Page 40

86

Polysubstituted 3- trifluoro methylpy razoles: regiose lective (3+2)- cycloaddition of trifluo roacetonitrile imines with enol ethers and
functional group transformations

By: Utecht, Greta; et al

Organic & Biomolecular Chemistry (2018), 16(8), 1252-1257.

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31-142-CAS-22170148 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 30 min, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C; 10 min, - 78 °C

1.3 Reagents: Ammonium chloride
Solvents: Water; -78 °C → rt
Experimental Protocols

87

Imidazopyridines, imidazop yrazines and imidazot riazines as PI3Kγ inhibitors and their prepar ation

By: Buesking, Andrew W.; et al

World Intellectual Property Organization, WO2017223414 A1 2017-12-28

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31-142-CAS-22121861 Steps: 1

1.1 Reagents: Potassium acetate

Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct
Solvents: Tetrahydrofuran; 100 min, 140 °C; 60 min, 140 °C

88

Fused pyrazole derivatives as J AK inhibitors and their prepar ation

 SciFinderⁿ® Page 41

By: Vidal Gispert, Laura; et al

World Intellectual Property Organization, WO2017220431 A1 2017-12-28

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31-142-CAS-18748569 Steps: 1 Yield: 57%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 5 min, - 60 °C

1.2 Reagents: Triisopropyl borate; 1 h, rt

1.3 Reagents: Acetic acid; 1 h, rt

89

Preparation of substituted pyrazoles and imidazoles as hemoglobin modifier compounds and uses thereof

By: Jin, Bohan; et al

World Intellectual Property Organization, WO2017218960 A1 2017-12-21

available View 8 Related Reactions

31-142-CAS-22161341 Steps: 1 Yield: 81%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C; 0.5 h, - 78 °C; 18 h, - 78 °C → rt

1.3 Reagents: Sodium chloride
Solvents: Water; rt
1.4 Reagents: Hydrochloric acid
Solvents: Water; pH 5 - 6, rt

90

Preparation of pyrazolo[1,5- a]pyrazin-4- yl derivatives

By: Brown, Matthew Frank; et al

United States, US20170240552 A1 2017-08-24

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 SciFinderⁿ® Page 42

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31-142-CAS-18577966 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 10 min, - 70 °C

1.2 1 h, -70 °C; - 70 °C → 20 °C

91

Preparation of azole- substituted pyridine compounds for inhibition of 20- HETE-producing enzyme

By: Tanaka, Hiroaki; et al

World Intellectual Property Organization, WO2017141927 A1 2017-08-24

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31-614-CAS-30785125 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; overnight, - 78 °C → rt

1.3 Solvents: Acetic acid; 2 h, rt; 2 h, rt; 1.5 h, rt

92

Utilization of an Active Site Mutant Receptor for the Identif ication of Potent and Selective Atypical 5- HT2C Receptor Agonists

By: Carpenter, Joseph; et al

Journal of Medicinal Chemistry (2017), 60(14), 6166-6190.

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31-142-CAS-17597982 Steps: 1 Yield: 100%

 SciFinderⁿ® Page 43

1.1 Reagents: Lithium diisopropylamide

Solvents: Tetrahydrofuran; -78 °C; 5 min, - 78 °C

1.2 30 min, - 78 °C
1.3 Solvents: Water; -78 °C → 0 °C
1.4 Reagents: Acetic acid; pH 6 - 7
Experimental Protocols

93

Preparation of 2- anilino-4- heteroaryl pyrimidine compounds as selective E GFR tyrosine kinase inhibitors for treatment of cancer

By: Song, Yuntao; et al

World Intellectual Property Organization, WO2017120429 A1 2017-07-13

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31-614-CAS-25775937 Steps: 1 Yield: 25%

1.1 Reagents: Butyllithium

Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium
Solvents: Tetrahydrofuran; 1 h, - 50 °C; - 50 °C

1.2 Reagents: Triisopropyl borate; 10 min, - 50 °C

1.3 Reagents: Acetic acid; 4 h, rt
1.4 Reagents: Sodium bicarbonate
Solvents: Water; rt

94

Discovery of GBT440, an Orally Bioava ilable R- State Stabilizer of Sickle Cell Hemoglobin

By: Metcalf, Brian; et al

ACS Medicinal Chemistry Letters (2017), 8(3), 321-326.

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31-142-CAS-21379402 Steps: 1
 SciFinderⁿ® Page 44

1.1 Reagents: Butyllithium, N ,N ,N ′, N ′-Tetramethylethylenediamine

Solvents: Tetrahydrofuran; 0 °C; 30 min, 0 °C

1.2 Reagents: Triisopropyl borate; 0 °C → rt; 3 h, rt

1.3 Reagents: Methanol
Experimental Protocols

95

Preparation of pyrazole derivatives useful as 5- lipoxygenase activating protein (F LAP) inhibitors

By: Broddefalk, Johan Olof; et al

World Intellectual Property Organization, WO2016177703 A1 2016-11-10

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31-614-CAS-27312409 Steps: 1 Yield: 91%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 10 min, - 78 °C

1.2 Reagents: Triisopropyl borate; 15 min, - 78 °C; 15 min, - 78 °C; - 78 °C → rt

1.3 Reagents: Acetic acid; overnight, rt

96

Preparation of N-[3-[[4- (2-pyridyl)pyrimidin- 2- yl]amino]phenyl]- 4- [(piperazin-1- yl)methyl] benzamide derivatives as inhibitors of

kinases

By: Werner, Milton H.; et al

World Intellectual Property Organization, WO2016172528 A1 2016-10-27

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97

Process for the preparation of androgen receptor antago nists and intermediates thereof

By: Laitinen, Ilpo; et al

 SciFinderⁿ® Page 45

World Intellectual Property Organization, WO2016162604 A1 2016-10-13

available

Suppliers (87) Suppliers (128) Suppliers (98)

31-142-CAS-16352395 Steps: 1 Yield: 68%

1.1 Reagents: Butyllithium

Solvents: Toluene, Tetrahydrofuran, Hexane; 2 - 3 h, 0 - 5 °C; 1 h, 0 - 5 °C

1.2 Reagents: Triisopropyl borate; 45 min, 0 - 5 °C; 5 °C → rt; 1 - 2 h, rt

1.3 20 - 30 min, rt; 45 min, rt; rt → 0 °C
1.4 Reagents: Acetic acid; 0.5 h, 0 - 5 °C; 5 °C → rt; 12 - 14 h, rt; rt → 0 °C
1.5 Solvents: Water; 0.5 h, 0 - 5 °C; 5 °C → rt; 0.5 h, rt

98

New pyrazole derivatives as N IK inhibitors and their prepar ation

By: Hynd, George; et al

World Intellectual Property Organization, WO2016062791 A1 2016-04-28

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31-142-CAS-15883378 Steps: 1

1.1 Reagents: Diisopropylethylamine

Solvents: Dichloromethane; 1.5 h, rt

99

Compositions and methods of prepar ation of substituted indole compounds as Trk A kinase inhibitors

By: Cooke, Andrew J.; et al

World Intellectual Property Organization, WO2016054807 A1 2016-04-14

 SciFinderⁿ® Page 46

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31-142-CAS-15970572 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 30 h, - 78 °C

1.2 -78 °C; 3 h, - 78 °C

1.3 Reagents: Hydrochloric acid
Solvents: Water; -78 °C

100

Preparation of pyrazolylc arboxamide derivatives for use as C RAC inhibitors

By: Ritter, Stefanie; et al

World Intellectual Property Organization, WO2015197188 A1 2015-12-30

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31-142-CAS-16479986 Steps: 1 Yield: 80%

1.1 Reagents: 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium
Solvents: Pentane; 20 min, rt

1.2 Solvents: Pentane, Tetrahydrofuran; 3 d, rt

101

Preparation of pyrazolylc arboxamide derivatives for use as C RAC inhibitors

By: Voss, Felix; et al

World Intellectual Property Organization, WO2015197187 A1 2015-12-30

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 SciFinderⁿ® Page 47

Suppliers (72) Suppliers (65) Suppliers (21)

31-142-CAS-15653044 Steps: 1 Yield: 80%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Pentane; 20 min, rt

1.2 Solvents: Pentane, Tetrahydrofuran; 3 d, rt

102

Preparation of halogen-substituted pyrazoles as pest- control agents

By: Bretschneider, Thomas

World Intellectual Property Organization, WO2015193218 A1 2015-12-23

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31-142-CAS-9287851 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 10 min, - 78 °C; 45 min, - 78 °C

1.2 Solvents: Tetrahydrofuran; 10 min, - 78 °C; 1.5 h, - 78 °C; 1 h, - 78 °C → rt

1.3 Reagents: Acetic acid; rt
Experimental Protocols

103

Preparation of benzodioxoles and other hetero cyclic compounds as therap eutic modulators of intrace llular calcium

By: Whitten, Jeffrey P.; et al

United States, US20150322012 A1 2015-11-12

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 SciFinderⁿ® Page 48

31-142-CAS-21286402 Steps: 1 Yield: 84%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 4 h, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C → rt; overnight, rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; 0.5 h, rt

104

Compounds that modulate intrace llular calcium

By: Rogers, Evan; et al

United States, US20150246909 A1 2015-09-03

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105

Preparation of pyrazolyl- based carbox amides useful as calcium release activated calcium channel (I CRAC) inhibitors

By: Nordhoff, Sonja; et al

World Intellectual Property Organization, WO2015090580 A1 2015-06-25

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31-142-CAS-2470711 Steps: 1 Yield: 80%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Pentane; 20 min, rt

1.2 Solvents: Pentane, Tetrahydrofuran; 3 d, rt

106

Preparation of pyridinyl- substituted pyrazolyl carbox amides useful as I CRAC inhibitors

By: Voss, Felix; et al

United States, US20150166505 A1 2015-06-18

 SciFinderⁿ® Page 49

available View 4 Related Reactions

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31-142-CAS-10249781 Steps: 1 Yield: 90%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Pentane; 20 min, 23 °C

1.2 Solvents: Pentane, Tetrahydrofuran; 3 d, 23 °C

107

Multidirectional Synthesis of Substi tuted Indazoles via Iridium- Catalyzed C-H Borylation

By: Sadler, Scott A.; et al

Journal of Organic Chemistry (2015), 80(10), 5308-5314.

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31-142-CAS-4046846 Steps: 1

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: tert-Butyl methyl ether; 2 h, 80 °C

Experimental Protocols

108

A method for preparing 3- trifluorom ethylpyrroleboronic acid

By: Tang, Yongjun; et al

China, CN104478911 A 2015-04-01

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31-142-CAS-18228109 Steps: 1 Yield: 72%

 SciFinderⁿ® Page 50

1.1 Reagents: Lithium diisopropylamide

Solvents: Tetrahydrofuran; -78 °C; 2 h, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C; - 78 °C → rt; 12 h, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; rt

109

Selective Haloge nation Using an Aniline Catalyst

By: Samanta, Ramesh C.; et al

Chemistry - A European Journal (2015), 21(34), 11976-11979.

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31-084-CAS-7301911 Steps: 1 Yield: 99%

1.1 Reagents: Chlorosuccinimide

Catalysts: 2,4,6-Trimethylaniline
Solvents: Dichloromethane; 24 h, rt

Experimental Protocols

110

CFBSA: a novel and practical chlori nating reagent

By: Lu, Zehai; et al

Chemical Communications (Cambridge, United Kingdom) (2015), 51(80), 14852-14855.

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31-084-CAS-3301049 Steps: 1 Yield: 89%

1.1 Reagents: N -Chloro-N -fluorobenzenesulfonamide

Solvents: Acetonitrile; overnight, rt

Experimental Protocols

111

Preparation of imidazopyr rolidinone derivatives as BET protein modulators useful in treating cancer

By: Blank, Jutta; et al

 SciFinderⁿ® Page 51

World Intellectual Property Organization, WO2014191894 A1 2014-12-04

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112

Benzimidazole derivatives as bromod omain inhibitors and their prepar ation

By: Aktoudianakis, Evangelos; et al

World Intellectual Property Organization, WO2014182929 A1 2014-11-13

available

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31-614-CAS-26574373 Steps: 1

1.1 Reagents: Potassium acetate

Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium
Solvents: 1,4-Dioxane; 2 h, 100 °C

113

Preparation of benzimidazolone derivatives as bromod omain inhibitors

By: Aktoudianakis, Evangelos; et al

World Intellectual Property Organization, WO2014160873 A1 2014-10-02

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31-142-CAS-18295363 Steps: 1
 SciFinderⁿ® Page 52

1.1 Reagents: Potassium acetate

Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium
Solvents: 1,4-Dioxane; 2 h, 100 °C

114

Preparation of tricyclic heterocycles as bet protein inhibitors

By: Combs, Andrew P.; et al

World Intellectual Property Organization, WO2014143768 A1 2014-09-18

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31-084-CAS-14359744 Steps: 1 Yield: 95%

1.1 Reagents: Chlorosuccinimide

Solvents: Tetrahydrofuran; 3 h, 70 °C

115

Pyrazolecarboxamides as CRAC inhibitors and their prepar ation

By: Nordhoff, Sonja; et al

United States, US20140194443 A1 2014-07-10

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31-142-CAS-1336863 Steps: 1 Yield: 80%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Pentane; 20 min, rt

1.2 Solvents: Pentane, Tetrahydrofuran; 3 d, rt

116

Pyrazolecarboxamides as CRAC inhibitors and their prepar ation

By: Nordhoff, Sonja; et al

United States, US20140194452 A1 2014-07-10

available
 SciFinderⁿ® Page 53

Suppliers (72) Suppliers (68) Suppliers (37)

31-142-CAS-15088148 Steps: 1 Yield: 78%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: Pentane; 20 min, rt

1.2 Solvents: Pentane, Tetrahydrofuran; 3 d, rt

117

Preparation of pyrrolopyridine and pyrrolop yrazine compounds as C RAC channel modulators

By: Vidal Juan, Bernat; et al

European Patent Organization, EP2738172 A1 2014-06-04

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31-142-CAS-18244466 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C → rt; overnight, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; rt

118

Preparation of imidazopyridine derivatives as neurogenic agents useful in treating diseases

By: Ceccarelli, Simona M.; et al

World Intellectual Property Organization, WO2014082979 A1 2014-06-05

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 SciFinderⁿ® Page 54

31-142-CAS-8110450 Steps: 1 Yield: 85%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 1 h, - 78 °C

1.2 -78 °C; 1.5 h, - 78 °C; < 1 h, - 78 °C → rt

119

Preparation of triazolop yridazine compounds as antitumor agents

By: Engelhardt, Harald; et al

United States, US20140135336 A1 2014-05-15

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31-142-CAS-18271769 Steps: 1 Yield: 42%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 20 min, - 78 °C; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; 30 min, - 78 °C; 16 h, - 78 °C → rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 5, rt

120

Palau'chlor: A Practical and Reactive Chlori nating Reagent

By: Rodriguez, Rodrigo A.; et al

Journal of the American Chemical Society (2014), 136(19), 6908-6911.

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31-084-CAS-13016503 Steps: 1 Yield: 98%

1.1 Reagents: Methyl N -[(chloroamino)[(methoxycarbonyl)amino]methylene]carbamate

Solvents: Acetonitrile; 12 h, rt

Experimental Protocols

121

Organometallic compounds and organic light- emitting devices including it

By: Choi, Jong-Won; et al

 SciFinderⁿ® Page 55

United States, US20140117318 A1 2014-05-01

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31-142-CAS-15513996 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; rt; 1 h, rt; rt → - 78 °C

1.2 -78 °C; 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

122

Preparation of N-heterocyclyl amides that modulate intrace llular calcium channels

By: Rogers, Evan; et al

World Intellectual Property Organization, WO2014059333 A1 2014-04-17

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31-142-CAS-6593864 Steps: 1 Yield: 100%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 4 h, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C → rt; overnight, rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; 0.5 h, rt

123

Preparation of benzimi dazoles as CN S active agents

By: Ceccarelli, Simona M.; et al

World Intellectual Property Organization, WO2014053409 A1 2014-04-10

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 SciFinderⁿ® Page 56

Suppliers (31) Supplier (1)

31-142-CAS-3442504 Steps: 1 Yield: 62%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; 1 h, - 78 °C; - 78 °C → rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 5, rt

124

Preparation of benzamide and heterobe nzamide compounds and antitumor agents

By: Edwards, Martin Paul; et al

World Intellectual Property Organization, WO2014049488 A1 2014-04-03

available

Suppliers (25) Suppliers (91) Suppliers (38)

31-142-CAS-9427744 Steps: 1 Yield: 47%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 2 h, rt; rt → - 65 °C

1.2 -655 °C; 15 min, - 65 °C; 1 h, 0 °C; overnight, rt; rt → 0 °C

1.3 Reagents: Ammonium chloride
Solvents: Water

125

Pyrazolo[3,4- d]pyrimidine compounds and their use as pde2 inhibitors and/or cyp3a4 inhibitors

By: Helal, Christopher John; et al

United States, US20140080806 A1 2014-03-20

available
 SciFinderⁿ® Page 57

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126

Iridium-Catalyzed C-H Borylation of Heteroa renes: Scope, Regiosele ctivity, Applic ation to Late-Stage Functionalization, and
Mechanism

By: Larsen, Matthew A.; et al

Journal of the American Chemical Society (2014), 136(11), 4287-4299.

Suppliers (128) Suppliers (144) Suppliers (29)

31-142-CAS-14178171 Steps: 1 Yield: 59%

1.1 Catalysts: 3,4,7,8-Tetramethyl-1,10-phenanthroline, Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium

Solvents: Tetrahydrofuran; 1 h, 80 °C

1.2 Solvents: Tetrahydrofuran; 16 h, 80 °C

1.3 Solvents: Diethyl ether, Water
Experimental Protocols

127

Cyclometalated pyrimidinylpyrazolate and pyrimid inyltriazolate metal complexes as phospho rescent materials for organic electrolu
minescent devices

By: Choi, Jong-Won; et al

European Patent Organization, EP2706064 A1 2014-03-12

available View 2 Related Reactions

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31-142-CAS-8530830 Steps: 1 Yield: 60%

 SciFinderⁿ® Page 58

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, rt

1.2 -78 °C; 15 min, - 78 °C; - 78 °C → 0 °C; 1 h, 0 °C

128

Synthesis of 3- aryl- 1H-indazoles via iridium- catalysed C-H borylation and Suzuki- Miyaura coupling

By: Egan, Ben A.; et al

RSC Advances (2014), 4(53), 27726-27729.

Suppliers (128) Suppliers (54) Suppliers (16)

31-142-CAS-1539184 Steps: 1 Yield: 96%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium, 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine

Solvents: tert-Butyl methyl ether; 1.5 h, 55 °C; 55 °C → rt

1.2 Solvents: Water; rt

Experimental Protocols

129

Synthesis of pinacol 1- methyl-1H-pyrazole-5- boronate

By: Zhang, Yu-juan; et al

Jingxi Huagong Zhongjianti (2013), 43(6), 27-28, 58.

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31-614-CAS-24248918 Steps: 1 Yield: 96%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; > 5 °C; 1 h, rt; rt → - 80 °C

1.2 Reagents: Trimethyl borate; -80 °C; 0.5 h, - 80 °C; - 80 °C → rt

1.3 Reagents: Ammonium chloride
Solvents: Water; neutralized, rt; 1 h, rt

130

Inhibitors of akt activity

By: Rouse, Meagan B.; et al

 SciFinderⁿ® Page 59

United States, US8592475 B2 2013-11-26

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131

Preparation of 3- pyrazolyl-2- pyridone derivatives as PDE10A inhibitors

By: Kanuma, Kosuke; et al

Japan, JP2013234123 A 2013-11-21

available

Suppliers (36) Suppliers (91)

31-142-CAS-22246721 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 30 min, < - 60 °C

1.2 30 min, < - 60 °C; 18 h, < - 60 °C → rt

132

Preparation of benzamide derivatives for inhibiting the activity of A BL1, A BL2 and B CR-ABL1 for treating cancer and viral infections

By: Furet, Pascal; et al

World Intellectual Property Organization, WO2013171642 A1 2013-11-21

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31-142-CAS-12338014 Steps: 1
 SciFinderⁿ® Page 60

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 10 min, - 70 °C; 10 min, - 70 °C

1.2 -70 °C; 1 h, - 70 °C; - 70 °C → rt

1.3 Reagents: Citric acid
Solvents: Water; pH 6
Experimental Protocols

133

Preparation of benzamide derivatives for inhibiting the activity of A BL1, A BL2 and B CR-ABL1 for treating cancer

By: Dodd, Stephanie Kay; et al

World Intellectual Property Organization, WO2013171639 A1 2013-11-21

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31-142-CAS-14145570 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 10 min, 70 °C; 10 min, 70 °C

1.2 70 °C; 1 h, 70 °C; 70 °C → rt

1.3 Reagents: Citric acid
Solvents: Water; pH 6
Experimental Protocols

134

Preparation of dihydropyr imidinone derivatives and their use as antiinfl ammatory agents

By: Shiro, Tomoya; et al

Japan, JP2013177318 A 2013-09-09

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31-614-CAS-29124825 Steps: 1

1.1 Solvents: Tetrahydrofuran; 7 h, rt

135
 SciFinderⁿ® Page 61

Some 2- pyrazinone derivatives and their use as inhibitors of neutro phile elastase

By: Chapman, David; et al

United States, US8466284 B2 2013-06-18

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136

Preparation of isoindo linone and pyrrolopy ridinone derivatives as A K T inhibitors useful in the treatment of cancer

By: Huang, Taisheng; et al

World Intellectual Property Organization, WO2013056015 A1 2013-04-18

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31-142-CAS-7406382 Steps: 1 Yield: 91%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 0 °C; 1 h, rt; rt → - 78 °C

1.2 0.5 h, - 78 °C; 0.5 h, - 78 °C → 0 °C

1.3 Reagents: Hydrochloric acid, Sodium chloride
Solvents: Water; pH 6 - 7, 0 °C
Experimental Protocols

137

Inhibitors of akt activity

By: Seefeld, Mark Andrew; et al

United States, US8420690 B2 2013-04-16

available
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138

Discovery of novel α 1- adrenoceptor ligands based on the antipsy chotic sertindole suitable for labeling as P ET ligands

By: Joergensen, Morten; et al

Bioorganic & Medicinal Chemistry (2013), 21(1), 196-204.

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31-142-CAS-6535488 Steps: 1 Yield: 93%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 1 h, 0 °C; 1 h, < 7 °C; 3 h, rt

1.2 Reagents: Trimethyl borate; -70 - - 65 °C; - 65 °C → rt

1.3 Reagents: Ammonium chloride
Solvents: Water
Experimental Protocols

139

Ruthenium-Catalyzed α- (Hetero)Arylation of Saturated Cyclic Amines: Reaction Scope and Mechanism

By: Peschiulli, Aldo; et al

Chemistry - A European Journal (2013), 19(31), 10378-10387.

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31-142-CAS-63165 Steps: 1 Yield: 100%

1.1 Solvents: Toluene; 12 h, rt

 SciFinderⁿ® Page 63

140

Preparation of pyrazolop yrimidine derivatives for use as P DE2 and/or C YP3A4 inhibitors

By: Helal, Christopher J.; et al

World Intellectual Property Organization, WO2012168817 A1 2012-12-13

available

Suppliers (85) Suppliers (95)

31-142-CAS-4199654 Steps: 1 Yield: 93%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C; 1.5 h, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C → rt; overnight, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; < 10 °C
1.4 Reagents: Hydrochloric acid
Solvents: Water; pH 6
Experimental Protocols

141

Benzoxazepin compounds as selective P I3K p110 delta inhibitors and their prepar ation and use in the treatment of lipid kinase-
mediated disorders

By: Elliott, Richard; et al

World Intellectual Property Organization, WO2012126901 A1 2012-09-27

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31-142-CAS-13381296 Steps: 1 Yield: 52%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 30 min, - 78 °C

1.2 Reagents: Triisopropyl borate; 10 min, - 78 °C; 1 h, - 78 °C; 4 h, - 78 °C → rt

1.3 Reagents: Hydrochloric acid
Solvents: Water
Experimental Protocols

142
 SciFinderⁿ® Page 64

Synthesis method of 1- methyl-4- pyrazole borate pinacol ester

By: Huang, Ping; et al

China, CN102690281 A 2012-09-26

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31-142-CAS-734088 Steps: 1 Yield: 89%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; < -60 °C; 3 h, - 70 - - 60 °C

1.2 Reagents: Triisopropyl borate; < - 60 °C; 3 h, - 70 - - 60 °C; - 60 °C → rt; 12 h, rt; rt → 10 °C

1.3 Reagents: Ammonium chloride
Solvents: Water; 0 - 10 °C
1.4 Reagents: Hydrochloric acid
Solvents: Water; pH 5

143

Discovery of novel 1,2,4- thiadiazole derivatives as potent, orally active agonists of sphing osine 1- phosphate receptor subtype 1 (S1 P1
)

By: Ren, Feng; et al

Journal of Medicinal Chemistry (2012), 55(9), 4286-4296.

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31-614-CAS-30595717 Steps: 1 Yield: 68%

1.1 Reagents: Lithium diisopropylamide, Triisopropyl borate

Solvents: Tetrahydrofuran; 5 min, - 78 °C; - 78 °C → rt; 1 h, rt

1.2 Reagents: Acetic acid; overnight, rt

Experimental Protocols

144

Preparation of 3- pyrazolyl-2- pyridone derivatives as PDE10A inhibitors

By: Kanuma, Kosuke; et al

World Intellectual Property Organization, WO2012029326 A1 2012-03-08

available
 SciFinderⁿ® Page 65

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31-142-CAS-6554226 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 30 min, < - 60 °C

1.2 30 min, < - 60 °C; 18 h, < - 60 °C → rt

145

Thiazole and thiophene deriva tives as store-operated calcium channels modulators and their prepar ation and use for treatment of S
OC channel- mediated diseases

By: Whitten, Jeffrey P.; et al

World Intellectual Property Organization, WO2012027710 A2 2012-03-01

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31-142-CAS-6873075 Steps: 1 Yield: 82%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 4 h, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C → rt; overnight, rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; 0.5 h, rt
Experimental Protocols

146

Preparation of heterocyclic compounds for treatment of schizop hrenia

By: Taniguchi, Takahiko; et al

World Intellectual Property Organization, WO2012020780 A1 2012-02-16

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31-142-CAS-6074172 Steps: 1

1.1 Solvents: Toluene; rt; 2 d, 40 °C

147

2- Pyrazinone derivatives for the treatment of disease or condition in which inhibition of neutrophil elastase activity is beneficial

By: Hansen, Peter; et al

United States, US8114881 B2 2012-02-14

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148

Preparation of fused heterocyclic compounds as P DE10A inhibitors

By: Hasui, Tomoaki; et al

World Intellectual Property Organization, WO2012018058 A1 2012-02-09

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31-142-CAS-14904904 Steps: 1

1.1 Solvents: Toluene; rt; 2 d, 40 °C

149
 SciFinderⁿ® Page 67

Preparation of heterocyclic compounds as phosphodi esterase 10A inhibitors for treatment of schizop hrenia

By: Yoshikawa, Masato; et al

World Intellectual Property Organization, WO2012018059 A1 2012-02-09

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31-142-CAS-7010726 Steps: 1

1.1 Solvents: Toluene; rt; 2 d, 40 °C

150

Preparation of sulfon amide derivatives as Nav1.7 inhibitors

By: Brown, Alan Daniel; et al

World Intellectual Property Organization, WO2012007868 A2 2012-01-19

available

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31-142-CAS-2786898 Steps: 1 Yield: 64%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 5 min, - 78 °C; 1 h, - 78 °C

1.2 -78 °C; 16 h, - 78 °C → rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; 1.5 h, rt
Experimental Protocols

151

Preparation of dihydropyr imidinone derivatives and their use as antiinfl ammatory agents

By: Shiro, Tomoya; et al

World Intellectual Property Organization, WO2012002502 A1 2012-01-05

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 SciFinderⁿ® Page 68

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31-142-CAS-1886234 Steps: 1

1.1 Solvents: Tetrahydrofuran; 7 h, rt

152

An innovative and efficient synthesis of stable isotope labelled 1- methyl-5- (4, 4,5,5- tetramethyl-1,3,2- dioxaborolan- 2- yl)- 1H-pyrazole
via [ 13 C42H3] N- methylp yrazole

By: Manning, Calvin; et al

Journal of Labelled Compounds and Radiopharmaceuticals (2012), 55(13), 467-469.

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31-031-CAS-14931583 Steps: 1 Yield: 80%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 1 min, 0 °C

1.2 6 h, 0 °C → rt; rt → 0 °C
1.3 Reagents: Butyllithium
Solvents: Hexane; 0 °C; 1 h, 0 °C → rt; rt → - 78 °C
1.4 15 min, - 78 °C; - 78 °C → rt; overnight, rt

153

Azolopyrimidine compounds as kinase inhibitors and their prepar ation and use in the treatment of diseases and methods

By: Hammond, Marlys; et al

World Intellectual Property Organization, WO2011149827 A1 2011-12-01

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 SciFinderⁿ® Page 69

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31-142-CAS-8672201 Steps: 1 Yield: 77%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, rt; rt → - 78 °C

1.2 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

Experimental Protocols

154

Preparation of aryl and hetero cyclic carbox amide compounds as therap eutic modulators of intrace llular calcium

By: Whitten, Jeffrey P.; et al

World Intellectual Property Organization, WO2011139765 A2 2011-11-10

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31-142-CAS-8878994 Steps: 1 Yield: 63%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 4 h, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C → rt; overnight, rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; 0.5 h, rt
Experimental Protocols

155

Preparation of benzodioxoles and other hetero cyclic compounds as therap eutic modulators of intrace llular calcium

By: Whitten, Jeffrey P.; et al

United States, US20110263612 A1 2011-10-27

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31-142-CAS-9196927 Steps: 1 Yield: 84%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 4 h, - 78 °C

1.2 Reagents: Trimethyl borate; -78 °C → rt; overnight, rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; 0.5 h, rt
Experimental Protocols

156

Preparation of polymorphic forms of cyanopheny lpyrazolylmethyloxotrifluoro methylphenyldihydropyrazine carboxylic acid

ethylamide derivatives for use as neutrophil elastase inhibitors

By: Cutting, Gary; et al

World Intellectual Property Organization, WO2011110852 A1 2011-09-15

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31-142-CAS-9400138 Steps: 1 Yield: 86%

1.1 Reagents: Butyllithium, 2,2,6,6-Tetramethylpiperidine

Solvents: Tetrahydrofuran, Hexane; < 0 °C; 30 min, 0 °C; 0 °C → - 50 °C

1.2 Solvents: Tetrahydrofuran; 10 min, < -50 °C; > 30 min, - 50 °C

1.3 25 min, < - 50 °C; 30 min, - 50 °C; - 50 °C → - 15 °C
1.4 Reagents: Acetic acid; 20 min, < 0 °C; 16 h, 0 °C → 20 °C; 20 °C → 0 °C
1.5 Reagents: Water; 35 min, < 0 °C; 30 min, < 0 °C
Experimental Protocols

157

Naphthyridine derivatives as T GFβ receptor kinase inhibitors and their prepar ation and use for the treatment of diseases

By: Jonczyk, Alfred; et al

World Intellectual Property Organization, WO2011101069 A2 2011-08-25

available
 SciFinderⁿ® Page 71

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31-031-CAS-12004480 Steps: 1

1.1 Reagents: Cesium carbonate

Solvents: Acetonitrile; 70 h, rt

Experimental Protocols

158

Inhibitors of akt activity

By: Rouse, Meagan B.; et al

United States, US20110160256 A1 2011-06-30

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159

Inhibitors of akt activity

By: Rouse, Meagan B.; et al

United States, US20110160255 A1 2011-06-30

available
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160

Inhibitors of akt activity

By: Lin, Hong; et al

United States, US20110098221 A1 2011-04-28

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161

Inhibitors of akt activity

By: Rouse, Meagan B.; et al

United States, US20110092423 A1 2011-04-21

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Product Only Reaction

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162
 SciFinderⁿ® Page 73

Preparation of pyrazole derivatives for treatment of C OPD

By: Alcaraz, Marie-Lyne; et al

World Intellectual Property Organization, WO2010094964 A1 2010-08-26

available

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31-142-CAS-4787096 Steps: 1

1.1 Reagents: Hexyllithium

Solvents: 2-Methylpentane, Tetrahydrofuran, Hexane; -5 °C

1.2 Solvents: Tetrahydrofuran; < 0 °C; 30 min, < 0 °C; < 0 °C → 25 °C

1.3 Reagents: Acetic acid
Solvents: Water; 30 min, 25 °C; 30 min, 25 °C
Experimental Protocols

163

Preparation of phenylalanine amide deriva tives useful for treating insulin- related diseases and conditions

By: Du, Xiaohui; et al

World Intellectual Property Organization, WO2010093849 A2 2010-08-19

available

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31-614-CAS-30546276 Steps: 1 Yield: 38%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 5 min, - 78 °C

1.2 Reagents: Triisopropyl borate; 90 min, - 78 °C → rt; 16 h, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; pH 7 - 8, rt
Experimental Protocols

164

Preparation of pyridazinone compounds as phosphodi esterase 10A inhibitors for preventing and treating schizop hrenia

By: Taniguchi, Takahiko; et al

United States, US20100197651 A1 2010-08-05

 SciFinderⁿ® Page 74

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31-142-CAS-7237508 Steps: 1 Yield: 76%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; 1 h, - 78 °C; - 78 °C → rt; overnight, rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 5
Experimental Protocols

165

Preparation of heteroarylsulfonamide derivatives for use as analgesics

By: Beaudoin, Serge; et al

World Intellectual Property Organization, WO2010079443 A1 2010-07-15

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31-142-CAS-7706091 Steps: 1 Yield: 78%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 15 min, 0 °C; 30 min, rt; rt → - 78 °C

1.2 -78 °C → rt; 60 h, rt

Experimental Protocols

166

Preparation of Pyrimidine derivative and pyridine derivative both having phosph atidyl inositol-3 kinase (P I3K) inhibitory activity

By: Taniyama, Daisuke; et al

World Intellectual Property Organization, WO2010061903 A1 2010-06-03

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31-614-CAS-29405124 Steps: 1

No Data Available

167

Preparation of pyrazolylthienylcarboxamide derivatives for use as A K T inhibitors

By: Rouse, Meagan B.; et al

World Intellectual Property Organization, WO2010045309 A1 2010-04-22

available

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31-142-CAS-9790109 Steps: 1 Yield: 77%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, rt; rt → - 78 °C

1.2 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

Experimental Protocols

168

Discovery of 1- [3-(4-Bromo-2- methyl-2H-pyrazol-3- yl)- 4- methoxyphenyl]- 3- (2, 4- difluorophenyl)urea (Nelotanserin) and Related 5-
Hydroxytryptami ne2A Inverse Agonists for the Treatment of Insomnia

By: Teegarden, Bradley R.; et al

Journal of Medicinal Chemistry (2010), 53(5), 1923-1936.

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31-142-CAS-2633544 Steps: 1 Yield: 60%

 SciFinderⁿ® Page 76

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; rt → - 78 °C; - 78 °C; 1.5 h, - 78 °C

1.2 overnight, -78 °C; - 78 °C → 0 °C

1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 6
Experimental Protocols

169

Alkyne [3 + 2] Cycload ditions of Iodosydnones Toward Functio nalized 1,3,5- Trisubstituted Pyrazoles

By: Browne, Duncan L.; et al

Journal of Organic Chemistry (2010), 75(3), 984-987.

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31-142-CAS-14657085 Steps: 1 Yield: 60%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 2 h, - 78 °C

1.2 2 h, -78 °C; - 78 °C → rt; 30 min, rt

1.3 Reagents: Ammonium chloride
Solvents: Water; rt
Experimental Protocols

170

Preparation of 3,4- diarylpyrazoles as protein kinase inhibitors

By: Pulici, Maurizio; et al

World Intellectual Property Organization, WO2010010154 A1 2010-01-28

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31-614-CAS-27338483 Steps: 1 Yield: 53%

 SciFinderⁿ® Page 77

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; < -70 °C; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; < - 70 °C; 2 h, - 70 °C → rt

1.3 Solvents: Tetrahydrofuran; 10 min, rt
1.4 Reagents: Acetic acid
Experimental Protocols

171

2- Isopropoxy-4,4,5,5- tetramethyl-1,3,2- dioxaborolane

By: Wood, Jessica L.; et al

e-EROS Encyclopedia of Reagents for Organic Synthesis (2010), 1-3.

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31-142-CAS-16788200 Steps: 1 Yield: 92%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C

1.2 -78 °C → rt

172

Hetero- pyrrole compounds as inhibitors of Akt activity for treatment of cancer and arthritis

By: Rouse, Meagan B.; et al

World Intellectual Property Organization, WO2009158376 A1 2009-12-30

available

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31-142-CAS-15213437 Steps: 1 Yield: 77%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, rt; rt → - 78 °C

1.2 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

Experimental Protocols

173
 SciFinderⁿ® Page 78

Preparation of thiazole and oxazole compounds as inhibitors of Akt activity useful in treatment of cancer and arthritis

By: Rouse, Meagan B.; et al

World Intellectual Property Organization, WO2009158374 A2 2009-12-30

available

Suppliers (85) Suppliers (91) Suppliers (107)

31-142-CAS-5328113 Steps: 1 Yield: 77%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, - 78 °C

1.2 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

Experimental Protocols

174

Hetero- pyrrole compounds as inhibitors of Akt activity for treatment of cancer and arthritis

By: Lin, Hong; et al

World Intellectual Property Organization, WO2009158373 A1 2009-12-30

available

Suppliers (85) Suppliers (91) Suppliers (107)

31-142-CAS-8098299 Steps: 1 Yield: 77%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, rt; rt → - 78 °C

1.2 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

Experimental Protocols

175

Inhibitors of AK T activity

By: Rouse, Meagan B.; et al

World Intellectual Property Organization, WO2009158372 A1 2009-12-30

available
 SciFinderⁿ® Page 79

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31-142-CAS-12905905 Steps: 1 Yield: 77%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, rt; rt → - 78 °C

1.2 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

Experimental Protocols

176

Pyrazole-substituted arylamide deriva tives and their use as P2 X3 and /or P2 X2/3 purinergic receptor antago nists and their prepar
ation and use in the treatment of diseases

By: Chen, Li; et al

World Intellectual Property Organization, WO2009077367 A1 2009-06-25

available View 9 Related Reactions

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31-031-CAS-3177023 Steps: 1

1.1 Reagents: Sodium hydride

Solvents: Dimethylformamide; rt; 1 h, rt

1.2 rt; 2 h, rt
1.3 Reagents: Water
1.4 Reagents: Butyllithium
Solvents: Tetrahydrofuran, Hexane; 30 min, - 78 °C; - 78 °C → 0 °C; 30 min, 0 °C
1.5 Reagents: Tributyl borate; 0 °C → - 78 °C; 1 h, - 78 °C; - 78 °C → rt; overnight, rt
1.6 Reagents: Ammonium chloride
Solvents: Water
Experimental Protocols

177

Trifluoromethyl-substituted pyridyl- and pyrazoly lboronic acids and esters: synthesis and Suzuki- Miyaura cross- coupling reactions

By: Clapham, Kate M.; et al

Organic & Biomolecular Chemistry (2009), 7(10), 2155-2161.

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31-142-CAS-12610138 Steps: 1 Yield: 98%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 30 min, - 78 °C

1.2 -78 °C; 1.5 h, - 78 °C; 1 h, - 78 °C → rt

1.3 Reagents: Acetic acid; rt

178

Preparation of 2- pyrazinone derivatives as inhibitors of neutrophil elastase

By: Ainge, Debra; et al

World Intellectual Property Organization, WO2009061271 A1 2009-05-14

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31-142-CAS-5789456 Steps: 1 Yield: 64%

1.1 Reagents: 2,2,3,3,4,4,5,5-Octafluoro-1-pentanol, Hexyllithium

Solvents: Tetrahydrofuran; 140 min, - 20 °C; 30 min, - 20 °C; - 20 °C → - 50 °C

1.2 Solvents: Tetrahydrofuran; 143 min, - 50 °C; 2.5 h, - 50 °C

1.3 66 min, - 50 °C
1.4 Reagents: Tetrahydrofuran; 45 min, - 50 °C; - 50 °C → - 15 °C
1.5 Reagents: Acetic acid; 45 min, - 15 °C; < 0 °C; 30 min, - 5 - 0 °C
1.6 Reagents: Water; 1.5 h, - 5 - 0 °C; 1 h, - 5 - 0 °C
Experimental Protocols

179

Azabicyclo [3.1.0]hexyl derivatives as modulators of dopamine D3 receptors and their prepar ation, pharmac eutical compos itions and
use in the treatment of diseases

By: Bertani, Barbara; et al

World Intellectual Property Organization, WO2009043883 A1 2009-04-09

available
 SciFinderⁿ® Page 81

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31-614-CAS-28723554 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 1 h, - 78 °C

1.2 Reagents: Bis(pinacolato)diborane; < - 75 °C; overnight, - 75 °C → rt

Experimental Protocols

180

Preparation of benzoxazinone deriva tives as inhibitors of long chain fatty acyl elongase (L CE)

By: Ishikawa, Shiho; et al

World Intellectual Property Organization, WO2009044788 A1 2009-04-09

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31-142-CAS-9100653 Steps: 1 Yield: 41%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 30 min, - 78 °C

1.2 Reagents: Triisopropyl borate; 1 h, - 78 °C

1.3 Reagents: Hydrochloric acid
Solvents: Water; 30 min, rt
Experimental Protocols

181

Preparation of pyrazole derivatives as inhibitors of A K T activity

By: Seefeld, Mark Andrew; et al

World Intellectual Property Organization, WO2008121786 A1 2008-10-09

available
 SciFinderⁿ® Page 82

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31-142-CAS-787246 Steps: 1 Yield: 77%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, rt; rt → - 78 °C

1.2 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

Experimental Protocols

182

Imidazolo-heteroaryl derivatives as Dlt A enzyme inhibitors and their prepar ation, pharmac eutical compos itions and use in the
treatment of bacterial infections

By: Escaich, Sonia; et al

World Intellectual Property Organization, WO2008117225 A2 2008-10-02

available View 5 Related Reactions

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31-614-CAS-29012888 Steps: 1

1.1 Reagents: Sodium hydride

Solvents: Tetrahydrofuran; 0 °C; overnight, rt

1.2 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0.5 h, - 78 °C
1.3 Reagents: Triisopropyl borate; 2 h, - 78 °C → rt
1.4 Reagents: Hydrochloric acid
Solvents: Water; pH 6, rt
Experimental Protocols

183

Preparation of novel heterocyclic carbox amides as inhibitors of Akt activity

By: Seefeld, Mark Andrew; et al

World Intellectual Property Organization, WO2008098104 A1 2008-08-14

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31-031-CAS-11336557 Steps: 1 Yield: 89%

1.1 Reagents: Sodium hydride

Solvents: Tetrahydrofuran; 0.5 h, rt

1.2 rt; 20 h, rt
1.3 Reagents: Butyllithium
Solvents: Hexane; 0 °C; 1 h, rt; rt → - 78 °C
1.4 15 min, - 78 °C; 1 h, - 78 °C → 0 °C
Experimental Protocols

184

Preparation of heterocyclic carbox amide compounds as inhibitors of Akt activity for treating arthritis and cancer

By: Seefeld, Mark Andrew; et al

World Intellectual Property Organization, WO2008098105 A1 2008-08-14

available

Suppliers (85) Suppliers (91) Suppliers (107)

31-142-CAS-10706040 Steps: 1 Yield: 76%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 0 °C; 1 h, rt; rt → - 78 °C

1.2 15 min, - 78 °C; 1 h, - 78 °C → 0 °C

1.3 Reagents: Ammonium chloride
Solvents: Water
Experimental Protocols

185

Preparation of macrocyclic amino acid derivatives as factor VIIa inhibitors useful as anticoa gulants
 SciFinderⁿ® Page 84

By: Wurtz, Nicholas Ronald; et al

World Intellectual Property Organization, WO2008079836 A2 2008-07-03

available

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31-142-CAS-8479952 Steps: 1 Yield: 27%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; 30 min, - 78 °C

1.2 -78 °C; overnight

Experimental Protocols

186

A Simple, Modular Method for the Synthesis of 3, 4,5- Trisubstituted Pyrazoles

By: McLaughlin, Mark; et al

Journal of Organic Chemistry (2008), 73(11), 4309-4312.

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31-614-CAS-27190727 Steps: 1 Yield: 82%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 5 min, - 60 - - 40 °C

1.2 Reagents: Triisopropyl borate; -40 °C; 1 h, - 40 °C → rt

1.3 Reagents: Acetic acid; 1 h, rt
Experimental Protocols

187

Preparation of oxazole, imidazole, and pyrazole boryl compounds using iridium complexes

By: Smith, Milton R.; et al

United States, US20080091027 A1 2008-04-17

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31-142-CAS-11143972 Steps: 1 Yield: 68%

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium

Solvents: Pentane; 10 - 15 min, rt

1.2 Catalysts: 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine; rt; 20 min, rt

1.3 Solvents: Diethyl ether; rt; 5 h, rt
Experimental Protocols

188

Preparation of 2- pyridone derivatives as neutrophil elastase inhibitors

By: Hansen, Peter; et al

World Intellectual Property Organization, WO2007129962 A1 2007-11-15

available

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31-142-CAS-10730274 Steps: 1

1.1 Reagents: Lithium diisopropylamide

Solvents: Ethylbenzene, Tetrahydrofuran, Hexane; 20 min, - 78 °C; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; 30 min, - 78 °C; overnight, - 78 °C → rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 5, rt
Experimental Protocols

189

Preparation of 2- pyrazinone derivatives as neutrophil elastase inhibitors

By: Hansen, Peter; et al

World Intellectual Property Organization, WO2007129963 A1 2007-11-15

available
 SciFinderⁿ® Page 86

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31-142-CAS-7111300 Steps: 1

1.1 Reagents: Lithium diisopropylamide

Solvents: Ethylbenzene, Tetrahydrofuran, Hexane; 20 min, - 78 °C; 1 h, - 78 °C

1.2 Reagents: Triisopropyl borate; 30 min, - 78 °C; overnight, - 78 °C → rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 5, rt
Experimental Protocols

190

Pyridyl amide deriva tives, processes for preparing them, pharmac eutical compos itions containing them, and their use as T- type
calcium channel antagonists

By: Barrow, James C.; et al

World Intellectual Property Organization, WO2007120729 A2 2007-10-25

available

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31-142-CAS-7329738 Steps: 1 Yield: 51%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 5 °C; 5 °C → rt; 1 h, rt; rt → - 78 °C

1.2 1 h, -78 °C
1.3 Reagents: Hydrochloric acid
Solvents: Water; -78 °C
1.4 Solvents: Pinacol, Tetrahydrofuran; 24 h, rt
Experimental Protocols

191

Preparation of fused heterocycles as mineralocorticoid receptor antago nists

By: Fukumoto, Shoji; et al

World Intellectual Property Organization, WO2007077961 A2 2007-07-12

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31-142-CAS-14873462 Steps: 1 Yield: 100%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 10 min, - 78 °C

1.2 Reagents: Triisopropyl borate; 30 min, - 78 °C; - 78 °C → - 15 °C

1.3 Reagents: Ammonium chloride
Solvents: Water; 1 h, rt
Experimental Protocols

192

A facile synthetic route to new pyrazolois oindolones

By: Gerard, Anne-Laure; et al

Tetrahedron Letters (2007), 48(23), 4123-4126.

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31-614-CAS-27420960 Steps: 1 Yield: 90%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -70 °C

1.2 Reagents: Triisopropyl borate; -70 °C

1.3 -
1.4 Reagents: Acetic acid

193

2- Isopropoxyl-4,4,5,5- tetramethyl-1,3,2- dioxaborolane

By: Wood, Jessica L.; et al

e-EROS Encyclopedia of Reagents for Organic Synthesis (2007), No pp. given.

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31-142-CAS-11584158 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; -78 °C → 22 °C

194

Efficient and simple synthesis of 3- aryl- 1H-pyrazoles

By: Gerard, Anne-Laure; et al

Tetrahedron Letters (2006), 47(27), 4665-4669.

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31-614-CAS-30718512 Steps: 1 Yield: 90%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -70 °C

1.2 Reagents: Triisopropyl borate; -70 °C

1.3 -70 °C
1.4 Reagents: Acetic acid; -70 °C

195

Preparation of diaryl and arylhet eroaryl urea derivatives, in particular pyrazoly lphenyl ureas, as 5- HT2A serotonin receptor
modulators

By: Teegarden, Bradley; et al

World Intellectual Property Organization, WO2005012254 A1 2005-02-10

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31-142-CAS-1244065 Steps: 1 Yield: 100%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran; rt → - 78 °C; - 78 °C; 1.5 h, - 78 °C

1.2 Reagents: Triisopropyl borate; overnight, - 78 °C → 0 °C

1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 6, 0 °C
Experimental Protocols

196
 SciFinderⁿ® Page 89

Synthesis of pinacol esters of 1- alkyl-1H-pyrazol-5- yl- and 1- alkyl-1H-pyrazol-4- ylboronic acids

By: Ivachtchenko, Alexandre V.; et al

Journal of Heterocyclic Chemistry (2004), 41(6), 931-939.

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31-142-CAS-9832819 Steps: 1 Yield: 90%

1.1 Solvents: Tetrahydrofuran; 2 h, rt

197

Preparation of diarylamine and arylhetero arylamine pyrazole derivatives as modulators of human 5 HT2A serotonin receptor

By: Teegarden, Bradley; et al

World Intellectual Property Organization, WO2004058722 A1 2004-07-15

available

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31-142-CAS-2968820 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; 30 min, - 78 °C; 1.5 h, - 78 °C

1.2 Reagents: Triisopropyl borate; -78 °C; overnight, - 78 °C; - 78 °C → rt

1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 6, rt

198

Preparation of pyrazolop yridines as kinase inhibitors

By: Villa, Manuela; et al

World Intellectual Property Organization, WO2004014374 A1 2004-02-19

available
 SciFinderⁿ® Page 90

Product Only Reaction

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No Data Available

199

Preparation of pyrrolopyrazoles as kinase inhibitors

By: Villa, Manuela; et al

World Intellectual Property Organization, WO2004013144 A1 2004-02-12

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Suppliers (3)

31-614-CAS-26793161 Steps: 1

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran, Hexane; -78 °C; 30 min, - 78 °C

1.2 Reagents: Borate(1-), hydrotris(1-methylethyl)-, potassium, ( T-4)-; -78 °C; - 78 °C → rt; 4.5 h, rt
1.3 Reagents: Hydrochloric acid
Solvents: Water; pH 6, rt

200

Preparation of 3,4- diarylpyrazoles as inhibitors of heat shock protein 90 (H SP90) and their use in the therapy of cancer

By: Drysdale, Martin James; et al

World Intellectual Property Organization, WO2003055860 A1 2003-07-10

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31-142-CAS-5750851 Steps: 1

1.1 Reagents: Butyllithium, 4-(4-Methoxyphenyl)-5-methyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole

Solvents: Tetrahydrofuran; -78 °C; 30 min, - 78 °C

1.2 Reagents: Triisopropyl borate; 45 min, - 78 °C → rt

1.3 Solvents: Water; rt

201

An efficient synthesis of tetra- substituted pyrazoles

By: Cottineau, Bertrand; et al

Synlett (2002), (5), 769-770.

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31-142-CAS-3953401 Steps: 1 Yield: 51%

1.1 Reagents: Butyllithium

Solvents: Tetrahydrofuran

1.2 Solvents: Tetrahydrofuran

1.3 Reagents: Ammonium chloride
Solvents: Water
Experimental Protocols

202

Preparation of 6- aryloxy-2- pyrazolylpyri(mi)dines as herbicides

By: Kleemann, Axel; et al

European Patent Organization, EP1108720 A1 2001-06-20

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31-142-CAS-21289136 Steps: 1

1.1 Reagents: Lithium diisopropylamide

Solvents: Tetrahydrofuran; -78 °C; 1 h, 10 °C; 10 °C → - 75 °C

1.2 Reagents: Trimethyl borate; 1 h, - 75 °C; overnight, rt

203

Cyclic HIV Protease Inhibi tors: Design and Synthesis of Orally Bioavai lable, Pyrazole P2/P2' Cyclic Ureas with Improved Potency
 SciFinderⁿ® Page 92

By: Han, Qi; et al

Journal of Medicinal Chemistry (1998), 41(12), 2019-2028.

Product Only Reaction

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Reaction Summary

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204

Cycloaddition of diazo compounds to ethylene boronic and acetylen eboronic esters

By: Matteson, Donald S.

Journal of Organic Chemistry (1962), 27, 4293-300.

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31-287-CAS-7045554 Steps: 1 Yield: 75%

No Data Available

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