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

HRID 520571Notes

Reaction equation

HRID 520571 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-indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of sodium hydride (60% in mineral oil) (0.677 g) in THF (25 ml) at 0° C. was added a solution of 6-bromo-3-fluoro-4-nitro-1H-indazole (4 g) in THF (25 ml) dropwise. The reaction mixture was allowed to stir for 30 min then allowed to warm to RT before benzenesulfonyl chloride (2.17 ml) was added. After approximately two hours the reaction mixture was partitioned between ethyl acetate and water. The layers were separated and the aq was then extracted again with ethyl acetate. The combined organics were then washed with brine, dried over magnesium sulphate, filtered and concentrated. The solid was triturated with methanol (50 ml) and filtered to yield the title compound, 5.96 g as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-cab6f2ae5e47464fada332e1a4921794
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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