2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

Base Information

Chemical Name:2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile
CAS No.:1312016-85-5
Molecular Formula:C₂₂H₂₃N₃O₂S
Molecular Weight:393.51
Hs Code.:

Synonyms:2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

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Chemical Property of 2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

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Technology Process of 2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

There total 14 articles about 2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1312016-84-4
2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

: 1312016-85-5
2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

: 1312021-14-9
2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

Guidance literature:: With Daicel IA-H; In hexanes; isopropyl alcohol; at 25 ℃; Resolution of racemate;

Reference yield:

: 1312021-02-5
6-acetylamino-5-trimethylsilanylethynyl nicotinic acid methyl ester

: 1312016-85-5
2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

: 1312021-14-9
2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

Guidance literature:: Multi-step reaction with 11 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C / Reflux

2.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C

2.2: 12.25 h / 0 - 25 °C

3.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C

3.2: 1 h / -78 °C

4.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

5.2: 1.5 h / -78 °C

6.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 2 h / 100 °C / Microwave irradiation

7.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 1 h / 100 °C

8.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 50 °C / 37503.8 Torr

9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 14 h / 20 °C

10.1: trichlorophosphate / chloroform / 3 h / 80 °C

11.1: Daicel IA-H / isopropyl alcohol; hexanes / 25 °C / Resolution of racemate

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; hydrogen; sodium carbonate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide; trichlorophosphate; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

: 1312017-82-5
1-benzenesulfonyl-2-(2-cyclopentyl-1-hydroxy-ethyl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

: 1312016-85-5
2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

: 1312021-14-9
2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbonitrile

Guidance literature:: Multi-step reaction with 8 steps

1.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

2.2: 1.5 h / -78 °C

3.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 2 h / 100 °C / Microwave irradiation

4.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 1 h / 100 °C

5.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 50 °C / 37503.8 Torr

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 14 h / 20 °C

7.1: trichlorophosphate / chloroform / 3 h / 80 °C

8.1: Daicel IA-H / isopropyl alcohol; hexanes / 25 °C / Resolution of racemate

With 4-methyl-morpholine; water; hydrogen; sodium carbonate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; lithium hexamethyldisilazane; trichlorophosphate; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol;