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

Base Information

• Chemical Name: 2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-fluoro-phenyl}-propan-2-ol
• CAS No.: 1312017-26-7
• Molecular Formula: C₂₃H₂₇FN₂O
• Molecular Weight: 366.479
• Mol file: 1312017-26-7.mol

Synonyms:

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

There total 10 articles about 2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-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:

4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-fluoro-benzoic acid methyl ester (1312019-80-9) + methylmagnesium chloride (676-58-4) → 2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-fluoro-phenyl}-propan-2-ol (1312017-26-7)

Guidance literature:

4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-fluoro-benzoic acid methyl ester; methylmagnesium chloride; In tetrahydrofuran; at 0 ℃; for 3h;

With water; ammonium chloride; In tetrahydrofuran; Product distribution / selectivity;

Reference yield:

1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone (1312018-67-9) → 2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-fluoro-phenyl}-propan-2-ol (1312017-26-7)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 1.5 h / -78 °C

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

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

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

5.1: tetrahydrofuran / 3 h / 0 °C

With tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; lithium hexamethyldisilazane; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; water;

Reference yield:

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (143141-23-5) → 2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-3-fluoro-phenyl}-propan-2-ol (1312017-26-7)

Guidance literature:

Multi-step reaction with 7 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

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; hexane; dichloromethane; water;

upstream raw materials:

1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone

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

methylmagnesium chloride

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