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

HRID 244709Notes

Reaction equation

HRID 244709 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]pyridine

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 to the reaction mixture. The reaction was stirred in the ice bath for 30 min and then allowed to warm up to room temperature. Water (30 mL) was added to the reaction mixture and the precipitate was collected by filtration to afford the title compound as an orange solid: mass (4.8 g).

Workup

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

Sources & evidence

ORD record
ord-f5c63c0f779749e18220f583e749cc54
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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