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

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To a mixture of Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)carbamate from Step D (0.39 g, 0.75 mmol), 2-methoxy-5-isopropylphenyl boronic acid (0.175 g, 0.90 mmol), and potassium carbonate (0.21 g, 1.50 mmol) in 4:1 acetone/water (10 ml), a catalytic amount of palladium acetate (10 mg) was added. The mixture was heated to and maintained at reflux for 2 h. TLC analysis (acetone/hexane=5:95) showed completion of the reaction. The acetone was removed under reduced pressure and the organic was extracted with methylene chloride (3×25 ml). The combined organic layers were washed with brine and dried over sodium sulfate. The title compound was obtained by flash column chromatography using 5:95 acetone/hexane as the eluant. NMR (CDCl3, 500 MHz) δ 8.20 (m, 2H), 7.75 (s, 1H), 7.48 (M, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.29 (m, 1H), 6.93 (m, 2H), 4.25-4.60 (m, 4H), 3.80 (m, 3H), 3.69 (s, 3H), 2.89 (m, 1H),1.20 (s, 6H). LC-MS (M+1) 585.4 (4.49 min).

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