Potassium Fluoride → Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-cyano-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

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A mixture of methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate (29 mg, 0.050 mmol), 2-cyanophenylboronic acid (10.9 mg, 0.074 mmol), potassium fluoride (8.7 mg, 0.149 mmol), 2-dicyclohexylphosphino(biphenyl) ligand (0.7 mg, 0.002 mmol) and a catalytic amount of palladium acetate was stirred in dioxane overnight at 80° C. The title compound was obtained by preparative thin layer chromatography using 20% EtOAc/hexane. 1H NMR (CDCl3, 600 MHz) δ 7.74 (m, 2H), 7.68 (d, J=7.8 Hz, 1H), 7.64 (t, J=7.8 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.52 (m, 3H), 7.39 (d, J=7.2 Hz, 1H), 7.24 (m, 1H), 4.30-4.55 (m, 4H), 3.71 (s, 3H). LC-MS (M+1) 561.0 (4.29 min).

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