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

HRID 905720Notes

Reaction equation

HRID 905720 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[CH:23]=[C:24]2[C:28](=[CH:29][C:30]=1[NH2:31])[NH:27][C:26](=[O:32])[CH2:25]2>>[NH2:31][C:30]1[CH:29]=[C:28]2[C:24]([C:25](=[CH:16][C:13]3[NH:12][C:9]4[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][N:3]([CH2:19][CH3:20])[CH2:1][CH3:2])[C:7](=[O:18])[C:8]=4[C:14]=3[CH3:15])[C:26](=[O:32])[NH:27]2)=[CH:23][C:22]=1[F:21]

Participants

3

Reactant 2

HCID 101035046-Amino-5-fluoroindolin-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 666072882-(6-Amino-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 61.8%

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 5-fluoro-6-amino-1,3-dihydro-indol-2-one (prepared according to J. Heterocylic Chem., 31, 1513, 1994) as starting materials to give 2-(6-amino-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (42 mg, 61.8%) as a red solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-92ed246a8d724849b6e6e643fc175c09
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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