Dichloromethane → 5-(2-Ethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 905873Notes

Reaction equation

C[N:2]([CH3:30])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[NH:11][C:12]([CH:15]=[C:16]3[C:24]4[C:19](=[CH:20]C=C(NC=O)[CH:23]=4)[NH:18][C:17]3=[O:28])=[C:13]([CH3:14])[C:7]=2[C:6]1=[O:29].F[C:32]([F:37])(F)[C:33](O)=O.Cl[CH2:39]Cl>>[CH2:30]([NH:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[NH:11][C:12]([CH:15]=[C:16]3[C:24]4[C:19](=[CH:20][CH:33]=[C:32]([F:37])[CH:23]=4)[NH:18][C:17]3=[O:28])=[C:13]([CH3:14])[C:7]=2[C:6]1=[O:29])[CH3:39]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 72526798N-{3-[5-(2-dimethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-5-yl}-formamide

Product 1

HCID 666075355-(2-Ethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 98%

Procedure

A stirred solution of ethyl-{2-[2-(6-fluoro-2-oxo-indan-1-ylidenemethyl)-3-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-5-yl]-ethyl}-carbamic acid tert-butyl ester (1.2 g, 2.5 mmol) obtained from Example 116 in dichloromethane (25 ml) was added dropwise slowly with 2.5 ml of trifluoroacetic acid. Upon the completion of the addition, the mixture was stirred for 2 hours at room temperature. The mixture was concentrated under reduced pressure to give 5-(2-ethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (0.94 g, 98%) as a yellow solid.

Workup

additionUpon the completion of the addition
concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-6e45b7d807eb4a368019ef835b07ced7
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012966B2

Reaction notes

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