Benzenesulfonyl chloride → 6-Bromo-1-(phenylsulfonyl)-1H-indazol-4-amine

HRID 1695723Notes

Reaction equation

HRID 1695723 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([NH2:13])[C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH:12]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([NH2:13])[C:7]2[CH:8]=[N:9][N:10]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 247280636-Bromo-1H-indazol-4-amine

Product 1

HCID 582558116-Bromo-1-(phenylsulfonyl)-1H-indazol-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To sodium hydride (1.886 g, 47.2 mmol) in DMF (10 ml) stirring at 0° C. was added a solution of 6-bromo-1H-indazol-4-amine (10 g, 47.2 mmol, available from Sinova) in DMF (30 ml) dropwise. NOTE-gas evolution. Upon complete addition the mixture was treated with benzene sulphonyl chloride (6.08 ml, 47.2 mmol) dropwise. The resulting mixture was stirred for 2 hrs at room temperature then the mixture was poured onto ice water (300 ml). The mixture was then extracted with ethyl acetate and the layers separated. The aqueous was re-extracted with ethyl acetate. The organics were then combined and washed with brine, dried over magnesium sulfate then filtered and evaporated to yield a brown gum that was triturated using DCM to yield the title compound as a peachy solid (8.72 g).

Workup

  1. additionUpon complete addition the mixture
  2. additionthe mixture was poured onto ice water (300 ml)
  3. extractionThe mixture was then extracted with ethyl acetate
  4. customthe layers separated
  5. extractionThe aqueous was re-extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationthen filtered
  9. customevaporated
  10. customto yield a brown gum that
  11. customwas triturated

Sources & evidence

ORD record
ord-62bf5c7da784429f877cea4d737bc00e
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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