2-Iodoaniline → HCID 16110631, compound

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Reaction Steps

2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)aniline. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (188 mg, 0.284 mmol) and 2-iodoaniline following General Procedure A. Flash chromatography (5-20% EtOAc/hexanes) yielded the title compound as a clear oil (122 mg, 90%): 1H NMR (CDCl3, 400 MHz) δ 7.48 (dd, 1H, J=6.4, 9.3 Hz), 7.29-7.25 (m, 2H), 7.21 (s, 1H), 7.18-7.13 (m, 4H), 6.84-6.80 (m, 1H), 6.77-6.75 (m, 1H), 4.85 (t, 1H, J=6.0 Hz), 3.81 (br s, 2H), 2.60 (t, 2H, J=7.5 Hz), 1.97-1.89 (m, 2H), 1.68-1.59 (m, 2H), 1.40-1.29 (m, 6H), 0.91 (s, 9H), 0.11 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 169.1, 155.2, 148.5, 147.9, 134.8, 133.5, 133.4, 132.5, 130.7, 127.8, 123.8, 121.9, 118.4, 73.8, 41.6, 41.1, 36.5, 34.3, 34.3, 30.9, 30.3, 23.3, 0.2, 0.0.

Provenance & Evidence