Potassium Hydroxide → 2-[5-methoxy-6-(2-hydroxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 490488Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15]C(=O)C)[N:8]([CH3:19])[CH:7]=[C:6]2[C:20]1[N:28](S(C2C=CC(C)=CC=2)(=O)=O)[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH:21]=1.[OH-].[K+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][OH:15])[N:8]([CH3:19])[CH:7]=[C:6]2[C:20]1[NH:28][C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH:21]=1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 67147540HCID 67147540, compound

Product 1

HCID 671475122-[5-methoxy-6-(2-hydroxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridineYield 32.6%

Procedure

2-[5-Methoxy-6-(2-hydroxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is prepared by following the procedure as described in example 89a, but using 0.5 g of 2-[5-methoxy-6-(2-acetyloxyethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 8.43 ml of a 5N aqueous potassium hydroxide solution. After purification by flash-pack chromatography (silica, 95/05 by volume dichloromethane/methanol as eluents, argon), 0.103 g of 2-[5-methoxy-6-(2-hydroxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is obtained, the characteristics of which are as follows:

Workup

custom2-[5-Methoxy-6-(2-hydroxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is prepared
customAfter purification by flash-pack chromatography (silica, 95/05 by volume dichloromethane/methanol as eluents, argon)

Sources & evidence

ORD record: ord-fccdf10098b14d4b93706ba6cbb91954
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

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