Water → 1H-Pyrrolo[2,3-B]pyridine, 5-bromo-4-chloro-1-(phenylsulfonyl)-

HRID 79524Notes

Reaction equation

HRID 79524 reaction equation
[Br:1][C:2]1[C:3]([Cl:11])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C>[Br:1][C:2]1[C:3]([Cl:11])=[C:4]2[CH:10]=[CH:9][N:8]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 457897885-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 497588851H-Pyrrolo[2,3-B]pyridine, 5-bromo-4-chloro-1-(phenylsulfonyl)-Yield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (0.50 g, 2.160 mmol) was placed in DMF (5 mL) at 0° C. NaH (0.10 g, 2.59 mmol) was then added, and the reaction was stirred for 20 minutes. Benzenesulfonyl chloride (0.304 mL, 2.38 mmol) was then added, and the reaction was stirred for 30 minutes at 0° C. Water (50 mL) was then added. The precipitate was filtered, washed with water, washed with ether, and dried to give 5-bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.8 g, 99.6% yield).

Workup

  1. stirringthe reaction was stirred for 30 minutes at 0° C
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-f2d475dee1154b489142c0efb993a9d0
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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