Potassium Carbonate → Methyl [3,5-bis(trifluoromethyl)benzyl][(4-fluoro-2'-methoxy-5'-methylbiphenyl-2-yl)methyl]carbamate

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A mixture of the Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)carbamate from Step B (0.02 g, 0.04 mmol), potassium carbonate (0.01 g, 0.08 mmol), 2-methoxy-5-methyl phenyl boronic acid (0.008 g, 0.05 mmol) and catalytic amount of palladium acetate (1 mg) in 4:1 acetone/water (2.5 ml) was heated to and maintained at reflux for 1 h. TLC analysis (acetone/hexane=5:95) showed no starting material. The solvent was removed under reduced pressure and the residue was extracted with methylene chloride (3×10 ml). The combined organic layers were washed with brine and dried over sodium sulfate. The title compound was obtained by preparative thin layer chromatography using acetone:hexane (5:95) as the eluant. 1H NMR (CDCl3, 500 MHz) δ 7.75 (s, 1H), 7.50 (s, 1H), 7.38 (s, 1H), 7.20 (m, 2H), 7.04 (m, 2H), 6.84 (s, 1H), 6.80 (m, 1H), 4.18-4.60 (m, 4H), 3.80 (s, 3H), 3.68 (s, 3H), 2.32 (s, 3H). LC-MS (M+1) 530.4 (4.43 min).

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