Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-indazole

HRID 244694Notes

Reaction equation

HRID 244694 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 223525484-bromo-1H-indazole

Product 1

HCID 583564014-Bromo-1-(phenylsulfonyl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirring suspension of NaH (0.78 g) in anhydrous THF (17.5 ml) at −5° C. was added 4-bromo-1H-indazole (3.5 g) in anhydrous THF (35 ml). Benzenesulfonyl chloride (2.5 ml) in anhydrous THF (17.5 ml) was added dropwise over 10 mins. The reaction was stirred for 1 h at 0° C. then quenched with water. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered and then evaporated to yield a solid residue that was triturated with methanol to give title compound, 5.18 g.

Workup

  1. customthen quenched with water
  2. customThe layers were separated
  3. extractionthe aqueous was re-extracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a solid residue that
  9. customwas triturated with methanol

Sources & evidence

ORD record
ord-0f0f703fc60344e0b129e6241dac3ee6
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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