Reaction Steps
2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)isonicotinonitrile. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (110 mg, 0.166 mmol) and 2-chloro-4-cyanopyridine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (72 mg, 75%): 1H NMR (CDCl3, 400 MHz) δ 8.79 (dd, 1H, J=5.0, 0.9 Hz), 7.84 (s, 1H), 7.74 (s, 1H), 7.43 (dd, 1H, J=5.0, 1.4 Hz), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 4.88 (dd, 1H, J=7.3, 6.6 Hz), 2.60 (t, 2H, J=7.8 Hz), 1.93 (m, 2H), 1.61 (m, 2H), 1.36 (m, 4H), 0.91 (s, 9H), 0.12 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 166.7, 150.8, 149.0, 148.6, 142.7, 128.3, 128.2, 127.1, 125.5, 123.7, 121.4, 120.2, 116.1, 68.6, 36.4, 35.8, 31.3, 29.0, 25.6, 25.6, 25.0, 18.1, −5.0, −5.2.
