Sodium hydride → 3-bromo-1-(2-chlorophenylsulfonyl)-1H-pyrazolo[4,3-c]pyridine

HRID 508195Notes

Reaction equation

HRID 508195 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][N:3]=1.[H-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](Cl)(=[O:22])=[O:21]>C1COCC1>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([S:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[Cl:13])(=[O:22])=[O:21])[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 761872-Chlorobenzenesulfonyl chlorideHCID 178419485HCID 178419485, compound

Product 1

HCID 681593183-bromo-1-(2-chlorophenylsulfonyl)-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-1H-pyrazolo[4,3-c]pyridine (198 mg, 1,0 mmol) in 10 ml THF was added portion wise at 0° C. sodium hydride (101 mg, 4 mmol, 95%). After addition was complete, 2-chlorobenzenesulfonyl chloride (495 mg, 2.347 mmol) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched by the addition of water. The product was extracted into ethyl acetate and the organic layer was washed with brine. The organic solvent was evaporated under reduced pressure to give 3-bromo-1-(2-chlorophenylsulfonyl)-1H-pyrazolo[4,3-c]pyridine as a yellow oil. The product was used in the next step without further purification.

Workup

  1. additionAfter addition
  2. customThe reaction mixture was quenched by the addition of water
  3. extractionThe product was extracted into ethyl acetate
  4. washthe organic layer was washed with brine
  5. customThe organic solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-21d16a97bfb642ac841ff566818ce3a4
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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