Potassium Hydroxide → HCID 67147545, compound

HRID 490427Notes

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

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 67147595HCID 67147595, compound

Product 1

HCID 67147545HCID 67147545, compoundYield 27.4%

Procedure

2-[1-(3-fluoropropyl)-5,6-dimethoxy-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is prepared by following the procedure described in example 88a, but using 0.042 g of 2-[5,6-dimethoxy-1-(3-fluoropropyl)indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 1.63 ml of a 5N aqueous potassium hydroxide solution. After purification by flash-pack chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents), 0.008 g of 2-[1-(3-fluoropropyl)-5,6-dimethoxy-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is obtained, the characteristics of which are as follows:

Workup

custom2-[1-(3-fluoropropyl)-5,6-dimethoxy-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is prepared
customAfter purification by flash-pack chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents)

Sources & evidence

ORD record: ord-c8806ea20c8e45d4af69371a7ecd1b50
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

Loading…