Water → Methyl 5-bromo-2'-cyano-4'-methylbiphenyl-3-carboxylate

Participants

Reaction Steps

Into a microwave vial were charged methyl 3-bromo-5-iodobenzoate (1.3 g, 3.8 mmol), 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.1 g, 4.6 mmol), cesium carbonate (3.1 g, 9.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (44q mg, 0.38 mmol), water (3 mL) and toluene (8 mL). The reaction mixture was subjected to microwave irradiation at 100° C. for 1 h. After cooling, the reaction was filtered and concentrated. The residue was purified by reversed phase HPLC (acetonitrile:water gradient) to the title compound as a white solid. LC-MS: 331.1 [M+1]+; 1H NMR (400 MHz, CDCl3): 8.16 (s, 1H), 8.03 (t, J=1.3 Hz, 1H), 7.76 (t, J=1.8 Hz, 1H), 7.53 (s, 1H), 7.33 (dd, J=1.6, 9.4 Hz, 1H), 7.25 (d, J=8.1 Hz, 1H), 3.93 (s, 3H), 2.43 (s, 3H).

Provenance & Evidence