Water → 4-(5-Cyano-7-cyclopropyl-1,3-benzoxazol-2-yl)-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide

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Reaction Steps

A mixture of 4-(7-bromo-5-cyano-1,3-benzoxazol-2-yl)-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide (EXAMPLE 113, Step A) (59 mg, 0.10 mmol), cyclopropylboronic acid (86 mg, 1.0 mmol), potassium carbonate (138 mg, 1.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) in dimethoxyethane (7 ml)/water (0.7 ml) was heated to reflux and stirred at this temperature for 4 d. The mixture was diluted with ethyl acetate, filtered, and concentrated. The residue was purified by flash column chromatography to afford the title compound. Mass spectrum (ESI) 547.2 (M+1). 1H NMR (500 MHz, DMSO-d6) δ: 8.77 (t, J=5.5 Hz, 1H), 8.65 (d, J=4.8 Hz, 1H), 8.31 (d, J=8.2 Hz, 2H), 8.18 (s, 1H), 8.08 (d, J=8.3 Hz, 2H), 7.56 (s, 1H) 6.96 (d, J=4.8 Hz, 1H), 5.74 (s, 1H), 4.65 (br d, J=12.6 Hz, 2H), 3.22 (t, J=6.2 Hz, 2H), 2.95 (t, J=12.4 Hz, 2H), 2.40 (m, 1H), 1.93 (m, 1H), 1.81 (br d, J=11.9 Hz, 2H), 1.15 (m, 5H).

Provenance & Evidence