Phenylacetyl isocyanate → N-(4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl carbamoyl)-2-phenylacetamide

Participants

Reaction Steps

A mixture of 308 (300 mg, 0.85 mmol) and 2-phenylacetyl isocyanate (164 mg, 1.02 mmoL) [Arthur J. Hill et al. JACS, 62; 1940; 1595] was stirred for 1 h at room temperature, loaded directly onto a flash chromatography column and gradient eluted with EtOAc, to MeOH/EtOAc (20:80) to afford the title compound 309a (45% yield) as a white solid. 1H NMR (d-DMSO) δ (ppm): 11.07 (s, 1H), 10.63 (s, 1H), 8.41(d, 1H, J=5.5 Hz), 7.94(d, 1H, J=1.4 Hz), 7.80(dd, 1H, J1=13.1 Hz, J2=2.4 Hz), 7.77(d, 1H, J=1.1 Hz), 7.65 (s, 1H), 7.46-7.39 (s, 2H), 7.35-7.19 (m, 4H), 7.28-7.24 (m, 1H), 6.54(dd, 1H, J1=5.5 Hz, J2=0.8 Hz), 4.03(q, 2H), 3.73 (s, 2H), 1.38(t, 3H). MS (m/z): 516.1 (M+H) (found).

Provenance & Evidence