Cesium carbonate → 6-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-1H-indole-3-carbonitrile

HRID 1618637Notes

Reaction equation

HRID 1618637 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=2)[N:17]=[C:16]([CH3:25])[C:15]=1[CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[CH:7][N:8]2[C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=3)[N:17]=[C:16]([CH3:25])[C:15]=2[CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 114700676-Bromo-1H-indole-3-carbonitrileHCID 609949634,6-Dichloro-2,3-dimethylquinoline

Product 1

HCID 672845396-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-1H-indole-3-carbonitrile (0.5 g, 2.26 mmol), 4,6-dichloro-2,3-dimethylquinoline (0.56 g, 2.49 mmol) and cesium carbonate (2.21 h, 6.79 mmol) in DMF (11.2 mL) was heated at 140° C. overnight. After this time the solvent was evaporated in vacuo and the residue was purified by flash column chromatography to give 6-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-1H-indole-3-carbonitrile as white solid. Mass Spectrum (ESI) m/e=411 (M+1).

Workup

  1. customAfter this time the solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-8b236d781f3a4192985099a7eddf83d2
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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