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

HRID 490486Notes

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][CH3:16])[N:8]([CH3:17])[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+]>>[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][CH3:16])[N:8]([CH3:17])[CH:7]=[C:6]2[C:18]1[NH:26][C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]=1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 67147655HCID 67147655, compound

Product 1

HCID 671476952-[5-methoxy-6-(2-methoxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridineYield 46.5%

Procedure

2-[5-Methoxy-6-(2-methoxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is prepared by following the procedure described in example 89a, but using 0.102 g of 2-[5-methoxy-6-(2-methoxyethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 0.80 ml of 5N potassium hydroxide. After purification by flash-pack chromatography (silica, 92.5/7.5 by volume dichloromethane/methanol as eluents, argon), 0.033 g of 2-[5-methoxy-6-(2-methoxyethoxy)-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-methoxyethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine is prepared
customAfter purification by flash-pack chromatography (silica, 92.5/7.5 by volume dichloromethane/methanol as eluents, argon)

Sources & evidence

ORD record: ord-042dd6f9a7bd4a139cebc36f8a73792c
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

Loading…