Potassium Hydroxide → [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-yl]methylamine

HRID 2426933Notes

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]([CH3:14])[CH:7]=[C:6]2[C:15]1[N:25](S(C2C=CC(C)=CC=2)(=O)=O)[C:18]2=[N:19][CH:20]=[CH:21][C:22]([CH2:23][NH2:24])=[C:17]2[CH:16]=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]([CH3:14])[CH:7]=[C:6]2[C:15]1[NH:25][C:18]2=[N:19][CH:20]=[CH:21][C:22]([CH2:23][NH2:24])=[C:17]2[CH:16]=1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 67147726HCID 67147726, compound

Product 1

HCID 67147534[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-yl]methylamineYield 27.3%

Procedure

[2-(5,6-Dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-yl]methylamine is prepared as described in Example 179a starting with 0.080 g of [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-yl]methylamine instead of the [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](4-trifluoromethylsulfanylbenzyl)amine used in Example 179a and 0.80 cm3 of 5N potassium hydroxide. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05 by volume as eluent), 0.015 g of [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-yl]methylamine is obtained, the characteristics of which are as follows:

Workup

custom[2-(5,6-Dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-yl]methylamine is prepared
customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05 by volume as eluent)

Sources & evidence

ORD record: ord-08fc1c39637748ca8937ca0645d542f0
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968566B2

Reaction notes

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