Dimethylformamide → 4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

HRID 520583Notes

Reaction equation

HRID 520583 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[H-].[Na+].CN(C=O)C.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:26])=[O:25])[CH:9]=[CH:10][C:3]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromo-1H-pyrrolo[2,3-b]pyridine (2 g) and sodium hydride (60% in mineral oil) (0.406 g) were added to DMF (30 ml) with stirring under nitrogen. After 15 min the reaction was cooled in an ice bath and benzenesulfonyl chloride (1.295 ml) was added. The reaction mixture was stirred in the ice bath for 30 min and then allowed to warm up to RT. Water (30 ml) was added and the precipitate collected by filtration to afford the title compound as an orange solid, 4.8 g.

Workup

  1. temperatureAfter 15 min the reaction was cooled in an ice bath
  2. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-ec9ffebc928f42bfa877041ff9b8da87
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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