4-(2,3-Difluoro-phenyl)-1,3-dihydro-indol-2-one → 5-(2-Diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 905767Notes

Reaction equation

HRID 905767 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=O)=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:18])[CH3:2].[F:21][C:22]1[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=1[C:29]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:30]=1[CH2:31][C:32](=[O:38])[NH:33]2>>[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=[C:31]3[C:30]4[C:34](=[CH:35][CH:36]=[CH:37][C:29]=4[C:23]4[CH:24]=[CH:25][CH:26]=[C:27]([F:28])[C:22]=4[F:21])[NH:33][C:32]3=[O:38])=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:18])[CH3:2]

Participants

3

Reactant 2

HCID 225619714-(2,3-Difluoro-phenyl)-1,3-dihydro-indol-2-oneHCID 250230155-(2-diethylaminoethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

Product 1

HCID 666066855-(2-Diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 22%

Procedure

The title compound was prepared under the same conditions as described in Example 1 with 5-(2-diethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde and 4-(2,3-difluoro-phenyl)-1,3-dihydro-indol-2-one (prepared according to WO2002055517) as starting materials to give 5-(2-diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (20 mg, 22.0%) as a yellow solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-79dd527c5c844e6892665d93205b9ea7
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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