Benzenesulfonyl chloride → 6-Bromo-3-fluoro-4-nitro-1-(phenylsulfonyl)-1H-indazole

HRID 244699Notes

Reaction equation

HRID 244699 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([F:13])=[N:9][NH:10]2)=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([F:13])=[N:9][N:10]2[S:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:25])=[O:24])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178526427HCID 178526427, compound

Product 1

HCID 583563926-Bromo-3-fluoro-4-nitro-1-(phenylsulfonyl)-1H-indazoleYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of sodium hydride (0.677 g, 16.92 mmol) in THF (25 ml) at 0° C. was added a solution of 6-bromo-3-fluoro-4-nitro-1H-indazole (4 g, 15.38 mmol) in THF (25 ml) dropwise. The reaction mixture was allowed to stir for 30 min then allowed to warm to room temperature before benzenesulfonyl chloride (2.170 ml, 16.92 mmol) was added. after approximately 2 h the reaction mixture was partitioned between ethyl acetate and water. The layers were separated and the aqueous was then extracted again with ethyl acetate. The combined organics were then washed with brine, dried over MgSO4, filtered and concentrated. The solid was triturated with 50 ml methanol and filtered to yield the title compound as a yellow solid (5.96 g).

Workup

  1. additionwas added
  2. customafter approximately 2 h the reaction mixture was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. extractionthe aqueous was then extracted again with ethyl acetate
  5. washThe combined organics were then washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe solid was triturated with 50 ml methanol
  10. filtrationfiltered

Sources & evidence

ORD record
ord-beb53c6c928f4e41b24b2ed903dc4f7d
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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