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

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Reaction Steps

A mixture of methyl [3,5-bis(trifluoromethyl)benzyl][(4-iodo-5′-isopropyl-2′-methoxybiphenyl-2-yl)methyl]carbamate from Example 10 (0.03 g, 0.045 mmol), potassium carbonate (0.012 g, 0.09 mmol), 3-pyridyl boronic acid (0.0066 g, 0.054 mmol) and a catalytic amount of palladium acetate (1 mg) in 4:1 acetone/water (2 ml) was heated to and maintained at reflux for 5 h. Acetone was removed and the organic 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 after preparative thin layer chromatography using 3:7 EtOAc/hexane as the eluant. 1H NMR (CDCl3, 500 MHz) δ 8.90 (m, 1H), 8.65 (m, 1H), 7.90 (m, 1H), 7.72 (s, 1H), 7.70 (m, 1H), 7.60 (dd, J=8.0, 2.5 Hz, 1H), 7.48 (m, 2H), 7.39 (d, J=8.0 Hz, 1H), 7.35 (s, 1H), 7.25 (m, 1H), 7.00 (s, 1H), 6.93 (d, J=8.0 Hz, 1H), 4.20-4.62 (m, 4H), 3.77 (s, 3H), 3.72 (s, 3H), 2.90 (m, 1H), 1.22 (s, 6H). LC-MS (M+1) 617.0 (3.76 min).

Provenance & Evidence