Potassium Carbonate → Methyl 3'-amino-4'-chloro-2-methylbiphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

(3-amino-4-chlorophenyl)boronic acid (1.0 g, 5.834 mmol), methyl 4-bromo-3-methylbenzoate (1.337 g, 5.834 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (476 mg, 0.583 mmol), aqueous potassium carbonate (11.57 mL, 1M, 11.57 mmol) and acetone (53 mL) were mixed and heated in a 70° C. oil bath for 1.5 hours to complete the coupling. Volatiles were removed from the crude mixture under reduced pressure. The resulting mixture was treated with water followed by ethyl acetate extraction. The combined extracts were dried over Na2SO4, filtrated and concentrated under reduced pressure to afford a dark oil. The resulting oil was purified by flash chromatography (SiO2, Biotage 40+M cartridge, 0-40% EtOAc in hexanes) to afford methyl 3′-amino-4′-chloro-2-methylbiphenyl-4-carboxylate. LCMS calc.=275.07; found=276.23 (M+1)+.

Provenance & Evidence