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

HRID 2096282Notes

Reaction equation

HRID 2096282 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]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of EXAMPLE 23E (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, and dried over high-vacuum for 16 hours to afford 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-6f3408bd8895499babd68a0014d796e5
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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