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

HRID 1615998Notes

Reaction equation

HRID 1615998 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)C=O.[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]pyridineYield 140.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromo-1H-pyrrolo[2,3-b]pyridine (2 g, 10.15 mmol) and sodium hydride (0.406 g, 10.15 mmol) were added to N,N-dimethylformamide (30 mL) with stirring and under nitrogen. After 15 minutes the reaction was cooled in an ice bath and benzenesulfonyl chloride (1.295 mL, 10.15 mmol) was added. The reaction mixture was stirred in the ice bath for 30 min and then allowed to warm up to room temperature. 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 minutes the reaction was cooled in an ice bath
  2. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-087cc71763604b73aff246b0577f1d56
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

Loading…