m-Chlorophenylhydrazine hydrochloride → 3-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

1-(3-Bromo-phenylsulfanyl)-propan-2-one (1.5 g, 6.12 mmol) and 3-chlorophenylhydrazine hydrochloride (1.21 g, 6.73 mmol) were combined in t-BuOH (50 mL) and the reaction was heated to 80° C. and stirred overnight. After cooling the reaction was worked-up using standard procedures to afford a crude mixture of two regioisomers which was then purified using silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound.

Provenance & Evidence