Sodium Carbonate → benzoic acid N'-[2-(4'-fluoro-biphenyl-2-ylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

Participants

Reaction Steps

A solution of benzoic acid N′-[2-(2-bromo-phenylsulfanyl)-acetyl]-N′-isopropyl-hydrazide (50 mg, 0.123 mmol) in DME (4 ml)/2M Na2CO3 (0.215 ml, 0.43 mmoles) was treated with 4-fluorophenylboronic acid (35 mg, 0.25 mmol) and Pd[PPh3]4 (14 mg, 0.012 mmol) for 12 hours at 90° C. The reaction mixture was partitioned between water and DCM. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was adsorbed on silica and purified on a silica gel column with a 20-50% ethyl acetate/hexane gradient. Further purification by RP HPLC afforded the product (9.5 mg, 20%). MS m/e 423.22 (M+H+)

Provenance & Evidence