Potassium Hydroxide → HCID 67147448, compound

HRID 2426822Notes

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][OH: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][CH3:13])[N:8]([CH2:14][CH2:15][CH2:16][OH: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 67147466HCID 67147466, compound

Product 1

HCID 67147448HCID 67147448, compoundYield 61.7%

Procedure

3-[5,6-Dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]propanol is prepared by following the procedure described in example 88a, but using 0.24 g of 3-[5,6-dimethoxy-3-(1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]propanol and a solution of 9.3 ml of methanolic potassium hydroxide (0.1 g/ml; 1.78M). After purification by flash-pack chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents), 0.103 g of 3-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)-indol-1-yl]propanol is obtained, the characteristics of which are as follows:

Workup

custom3-[5,6-Dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]propanol is prepared
customAfter purification by flash-pack chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents)

Sources & evidence

ORD record: ord-e1ee7c2c6fa34670ac910c768578788c
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968566B2

Reaction notes

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