Water → 3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2088987Notes

Reaction equation

HRID 2088987 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].O.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 455881343-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of Example 1a (25 g, 127 mmol) in N,N-dimethylformamide (200 mL) was slowly added sodium hydride (3.37 g, 133 mmol) over several minutes. After stirring for 30 minutes in the cold water bath, benzenesulfonyl chloride (17.18 ml, 133 mmol) was added via a syringe. The solution was allowed to warm to room temperature overnight, quenched slowly with 500 mL water, stirred for 30 minutes, and then filtered. The solid obtained was washed with water, followed by 300 mL of hexanes, dried over high-vacuum for 16 hours to give 34 g of the title compound which was used without further purification. MS (ESI+) m/z 338.7 (M+H)+.

Workup

  1. customTo a 0° C.
  2. customover several minutes
  3. additionwas added via a syringe
  4. customquenched slowly with 500 mL water
  5. filtrationfiltered
  6. customThe solid obtained
  7. washwas washed with water
  8. customdried over high-vacuum for 16 hours

Sources & evidence

ORD record
ord-c346156023db451e9104fa90a54f01bb
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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