Dimethylformamide → (5-Bromo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-phenyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 905775Notes

Reaction equation

HRID 905775 reaction equation
[O:1]=[C:2]1[C:7]2[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9](C=O)[NH:10][C:6]=2[CH2:5][CH2:4][NH:3]1.[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[CH2:23]2.N1CCCC[CH2:31]1.CN(C)C=O>C(O)C>[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[C:23]2=[CH:31][N:10]1[C:6]2[CH2:5][CH2:4][NH:3][C:2](=[O:1])[C:7]=2[C:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:9]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 6111935-Bromo-2-oxindoleHCID 866376804-oxo-3-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

Product 1

HCID 66608343(5-Bromo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-phenyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-oxo-3-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde (36 mg, 0.15 mmol), 5-bromo-1,3-dihydro-indol-2-one (33 mg, 0.146 mmol), piperidine (0.05 ml), N,N-dimethylformamide (0.05 ml) in anhydrous ethanol (0.75 ml) was heated to reflux for 2 hours and stirred at room temperature overnight. The resulting mixture was filtered to give (5-bromo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-phenyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (61 mg, 88%) as a yellow solid.

Workup

  1. temperatureto reflux for 2 hours
  2. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-f77c5fcd41674dfcbc45d887b2528b17
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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