3-Fluorophenylhydrazine hydrochloride → [3-(6-Fluoro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Participants

Reaction Conditions

Reaction Steps

[3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid (0.500 g, 2.2 mmol) and 3-fluorophenylhydrazine hydrochloride (0.400 g, 2.45 mmol) were dissolved in t-BuOH (10 mL). The reaction was stirred at 70° C. for 1.5 hours then submitted to aqueous workup. Purification by preparatory HPLC (10-100% ACN in H2O) afforded a 5:3 mixture of separable regioisomers of which the title compound was the major component.

Provenance & Evidence