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

Participants

Reaction Steps

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).

Provenance & Evidence