2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol

Base Information

• Chemical Name: 2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol
• CAS No.: 1312016-54-8
• Molecular Formula: C₂₅H₃₂N₂O₄S
• Molecular Weight: 456.606
• Mol file: 1312016-54-8.mol

Synonyms:2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol

Chemical Property of 2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol

There total 11 articles about 2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol 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:

2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (1312016-52-6) → 2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (1312016-54-8) + 2-{2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (1312021-08-1)

Guidance literature:

With Daicel IB-H; In hexanes; ethanol; at 25 ℃; Resolution of racemate;

Reference yield:

1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine → 2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (1312016-54-8) + 2-{2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (1312021-08-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: bromine; pyridine / dichloromethane / 2 h / 0 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C

4.1: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux

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

5.2: 12.25 h / 0 - 25 °C

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

6.2: 1 h / -78 °C

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

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

8.2: 1.5 h / -78 °C

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

10.1: boron tribromide / dichloromethane / 1 h / -78 - 20 °C

10.2: pH 6

11.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C

11.2: 1 h / 80 °C

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

13.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 50 °C / 2585.81 Torr

14.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 - 20 °C

15.1: Daicel IB-H / ethanol; hexanes / 25 °C / Resolution of racemate

With pyridine; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; bromine; sodium; boron tribromide; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

7-azaindoline (10592-27-5) → 2-{2-[2-cyclopentyl-1(R)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (1312016-54-8) + 2-{2-[2-cyclopentyl-1(S)-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propan-1-ol (1312021-08-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

1.2: 3 h / 0 °C

2.1: bromine; pyridine / dichloromethane / 2 h / 0 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C

5.1: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux

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

6.2: 12.25 h / 0 - 25 °C

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

7.2: 1 h / -78 °C

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

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

9.2: 1.5 h / -78 °C

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

11.1: boron tribromide / dichloromethane / 1 h / -78 - 20 °C

11.2: pH 6

12.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C

12.2: 1 h / 80 °C

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

14.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 50 °C / 2585.81 Torr

15.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 - 20 °C

16.1: Daicel IB-H / ethanol; hexanes / 25 °C / Resolution of racemate

With pyridine; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; bromine; sodium; boron tribromide; sodium hydride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

5-bromo-1H-pyrrolo[2,3-b]pyridine

5-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine

7-azaindoline

5-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine