To a solution of {5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methanol (intermediate B1.1, 0.03 g, 0.09 mmol) in 0.6 ml of THF was added 1M NaHMDS in THF (0.11 ml, 0.11 mmol). After 10 min at rt, 6-bromo-N-ethylnicotinamide (0.02 g, 0.08 mmol) was added. After 3 h, a drop of water was added to the reaction and purified by reverse phase HPLC to give 6-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)-N-ethylpyridine-3-carboxamide. 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=2.4 Hz, 1H), 8.35 (d, J=2.4 Hz, 1H), 8.08 (m, 2H), 7.96 (dd, J=8.6, 2.6 Hz, 1H), 7.48 (dd, J=8.4, 2.6 Hz, 1H), 7.13 (m, 2H), 6.96 (d, J=8.4 Hz, 1H), 6.8 (d, J=8.8 Hz, 1H), 5.94 (s, 1H), 5.48 (s, 2H), 3.46 (m, 2H), 1.24 (t, J=7.3 Hz, 3H); HRMS exact mass calc for C23H18ClFN4O3S [M+H]+: 485.0845; observed: 485.0854.
