2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

Base Information

Chemical Name:2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid
CAS No.:1312016-90-2
Molecular Formula:C₂₄H₂₇FN₂O₃
Molecular Weight:410.488
Hs Code.:

Synonyms:2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

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Chemical Property of 2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

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Technology Process of 2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

There total 16 articles about 2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid 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:

: 1312016-89-9
2-{2-cyclopentyl-1-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

: 1312016-90-2
2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

: 1312021-16-1
2-{2-cyclopentyl-1(S)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

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

Reference yield:

: 749928-52-7
2-(4-bromo-2-fluorophenyl)propan-2-ol

: 1312016-90-2
2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

: 1312021-16-1
2-{2-cyclopentyl-1(S)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 12 h / 20 °C

2.1: bis(pinacol)diborane; potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 3 h / 20 - 80 °C

2.2: 3 h / 100 °C

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

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

5.1: sodium hydroxide; water / tetrahydrofuran / 10 h / 70 °C

6.1: copper(II) choride dihydrate / ethanol / 3 h / 20 °C / Reflux

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

With copper(II) choride dihydrate; tetrabutyl ammonium fluoride; water; hydrogen; potassium acetate; pyridinium p-toluenesulfonate; bis(pinacol)diborane; sodium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexanes; ethanol; dichloromethane; dimethyl sulfoxide;

Reference yield:

: 849067-96-5
1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester

: 1312016-90-2
2-{2-cyclopentyl-1(R)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

: 1312021-16-1
2-{2-cyclopentyl-1(S)-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

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

1.2: 12.25 h / 0 - 25 °C

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

2.2: 1 h / -78 °C

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

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

4.2: 1.5 h / -78 °C

5.1: bis(pinacol)diborane; potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 3 h / 20 - 80 °C

5.2: 3 h / 100 °C

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

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

8.1: sodium hydroxide; water / tetrahydrofuran / 10 h / 70 °C

9.1: copper(II) choride dihydrate / ethanol / 3 h / 20 °C / Reflux

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

With copper(II) choride dihydrate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; hydrogen; potassium acetate; Dess-Martin periodane; bis(pinacol)diborane; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexanes; ethanol; dichloromethane; dimethyl sulfoxide;