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

HRID 490514Notes

Reaction equation

[CH:1]1([NH:4][CH2:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[C:13]([C:15]4[C:23]5[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=5)[N:17]([CH3:28])[CH:16]=4)=[CH:14][C:7]=23)[CH2:3][CH2:2]1.[OH-].[K+]>>[CH:1]1([NH:4][CH2:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[NH:12][C:13]([C:15]4[C:23]5[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=5)[N:17]([CH3:28])[CH:16]=4)=[CH:14][C:7]=23)[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 67147532HCID 67147532, compound

Product 1

HCID 67147491cyclopropyl[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amineYield 79.9%

Procedure

Cyclopropyl[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine is prepared as described in Example 179a starting with 0.06 g of cyclopropyl[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine 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 0.5 cm3 of 5N potassium hydroxide. 0.034 g of cyclopropyl[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine is obtained, the characteristics of which are as follows:

Workup

customCyclopropyl[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amine is prepared

Sources & evidence

ORD record: ord-c5ba7d7b8c4240d2bcc13d9b5e6a953f
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

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