Hydrochloric Acid → Methyl 3-acetyl-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-bromo-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate (880 mg, 2.32 mmol), 1-(vinyloxy)butane (464.7 mg, 0.6 mL, 4.64 mmol), palladium acetate (16.0 mg, 0.070 mmol), DPPP (63.1 mg, 0.0153 mmol) and potassium carbonate (382 mg, 2.78 mmol) in DMF (2.5 mL) and H2O (0.3 mL) in a Smith process vial was heated at 122° C. in microwave for 3 h. The reaction mixture was cooled down to RT and hydrolyzed by addition of 5% HCl slowly. The reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum. The crude mixture was purified by reverse phase prep HPLC to give the title compound (520 mg, 65.4% yield): HPLC retention time: 1.88 min (method A). MS (ESI) (M+H)+ 343.00.

Provenance & Evidence