2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol

Base Information

• Chemical Name: 2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol
• CAS No.: 1312021-21-8
• Molecular Formula: C₂₃H₂₇FN₂O
• Molecular Weight: 366.479
• Mol file: 1312021-21-8.mol

Synonyms:2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol

Chemical Property of 2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol

There total 6 articles about 2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-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-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol (1312017-27-8) → 2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol (1312021-21-8) + 2-{4-[2-cyclopentyl-1(R)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol (1312017-28-9)

Guidance literature:

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

Reference yield:

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (143141-23-5) → 2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol (1312021-21-8) + 2-{4-[2-cyclopentyl-1(R)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol (1312017-28-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C

1.2: 1 h / -78 °C

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

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

3.2: 1.5 h / -78 °C

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

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 25 °C

6.1: hydrogen / palladium 10% on activated carbon / methanol / 16 h / 50 °C / 2585.81 Torr

7.1: tetrahydrofuran / 3 h / 0 °C

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

With n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; Dess-Martin periodane; lithium hexamethyldisilazane; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; hexane; dichloromethane; water;

Reference yield:

4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-2-fluoro-benzoic acid methyl ester (1312019-81-0) → 2-{4-[2-cyclopentyl-1(S)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol (1312021-21-8) + 2-{4-[2-cyclopentyl-1(R)-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol (1312017-28-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 25 °C

2: hydrogen / palladium 10% on activated carbon / methanol / 16 h / 50 °C / 2585.81 Torr

3: tetrahydrofuran / 3 h / 0 °C

4: Daicel IA-H / ethanol; hexanes / 25 °C / Resolution of racemate

With tetrabutyl ammonium fluoride; hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexanes; ethanol;

upstream raw materials:

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine

methyl 4-bromo-2-fluorobenzoate

2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-phenyl}-propan-2-ol

4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-2-fluoro-benzoic acid methyl ester