Potassium Hydroxide → 2-{5,6-dimethoxy-1-[2-(4-methyl-piperazin-1-yl)ethyl]-1H-indol-3-yl}-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 490464Notes

Reaction equation

HRID 490464 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[CH:7]=[C:6]2[C:23]1[N:32](S(C2C=CC(C)=CC=2)(=O)=O)[C:26]2=[N:27][CH:28]=[C:29]([F:31])[CH:30]=[C:25]2[CH:24]=1.[OH-].[K+].ClCCl.CO>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]1)[CH:7]=[C:6]2[C:23]1[NH:32][C:26]2=[N:27][CH:28]=[C:29]([F:31])[CH:30]=[C:25]2[CH:24]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 21226129Dichloromethane methanolHCID 671474312-[5,6-dimethoxy-1-[2-(4-methylpiperazin-1-yl)ethyl]-1H-indol-3-yl]-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 116189992-{5,6-dimethoxy-1-[2-(4-methyl-piperazin-1-yl)ethyl]-1H-indol-3-yl}-5-fluoro-1H-pyrrolo[2,3-b]pyridineYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

But using 0.82 g of 2-[5,6-dimethoxy-1-[2-(4-methylpiperazin-1-yl)ethyl]-1H-indol-3-yl]-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine dissolved in 100 ml of methanol and 2 g of potassium hydroxide dissolved in 7 ml of water. After flash chromatography on a silica column [eluent: dichloromethane/methanol (70/30 by volume)], 0.37 g of 2-{5,6-dimethoxy-1-[2-(4-methyl-piperazin-1-yl)ethyl]-1H-indol-3-yl}-5-fluoro-1H-pyrrolo[2,3-b]pyridine is thus obtained in the form of a solid, the characteristics of which are as follows:

Sources & evidence

ORD record
ord-f6407a00617c4ed19352ee4917b30805
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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