Potassium Hydroxide → 2-(1-{2-[3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dimethoxyindol-1-yl]ethyl}piperidin-4-yl)ethanol

HRID 490441Notes

Reaction equation

HRID 490441 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][OH:34])[CH2:28][CH2:27]4)[CH:12]=3)=[CH:10][C:3]=12.[OH-].[K+].ClCCl.CO>CO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH2:24][CH2:25][N:26]4[CH2:27][CH2:28][CH:29]([CH2:32][CH2:33][OH:34])[CH2:30][CH2:31]4)[CH:12]=3)=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21226129Dichloromethane methanolHCID 671474712-[1-(2-{3-[4-chloro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxyindol-1-yl}ethyl)piperidin-4-yl]ethanol

Product 1

HCID 115113892-(1-{2-[3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dimethoxyindol-1-yl]ethyl}piperidin-4-yl)ethanolYield 64.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

But using 0.160 g of 2-[1-(2-{3-[4-chloro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxyindol-1-yl}ethyl)piperidin-4-yl]ethanol and 0.58 g of potassium hydroxide in 10 ml of methanol. After flash chromatography on a silica column [eluent: dichloromethane/methanol (80/20 by volume)], 0.078 g of 2-(1-{2-[3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dimethoxyindol-1-yl]ethyl}piperidin-4-yl)ethanol is thus obtained in the form of a solid, the characteristics of which are as follows:

Sources & evidence

ORD record
ord-d015cf6cff254b4fb633cd8b7e0ee9a2
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

Loading…