Water → 4-(2-Benzofuranyl)-2,8-bis(trifluoromethyl)quinoline

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A solution of 4-bromo-2,8-bis(trifluoromethyl)quinoline (500 mg, 1.45 mmol) in dry dimethoxyethane (10 mL) was treated with tetrakis(triphenylphosphine)palladium (2.3 mg, 10 mol %), stirred for 10 min, treated with benzofuran-2-boronic acid (235 mg, 1.45 mmol) and 2-M Na2CO3 solution (1.45 mL, 2.9 mmol) then refluxed for 2 h. The mixture was cooled, treated with water (10 mL), extracted with EtOAc (3×20 mL), the organic phase was washed with brine (20 mL), dried (MgSO4), concentrated in vacuo and the resulting yellow solid recrystallised from heptane to give the title compound (351 mg, 64%) as an off-white crystalline solid: mp 129-130° C.; IR νmax (Nujol)/cm−1 2924, 1592, 1463, 1314, 1145, 1116, 1010, 749 and 691; NMR δH (400 MHz, CDCl3) 7.35 (1H, t, J 7.1 Hz), 7.42-7.47 (2H, m), 7.65 (1H, d, J 7.5 Hz), 7.73 (1H, d, J 8.0 Hz), 7.80 (1H, t, J 7.9 Hz), 8.19-8.23 (2H, m) and 8.86 (1H, d, J 9.0 Hz).

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