Phenylacetyl isocyanate → N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamoyl)-2-phenylacetamide

Participants

Reaction Steps

A mixture of 306 (99 mg, 0.29 mmol) and 2-phenylacetyl isocyanate (97 mg, 0.60 mmoL) [A. 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 (10:90) to afford the title compound 307 (42% yield) as a white solid. 1H NMR (d-DMSO) δ (ppm): 11.11 (s, 1H), 10.68 (s, 1H, J=5.5 Hz), 8.49(d), 7.85 (s, 1H), 7.82(dd, 1H, J1=12.9 Hz, J2=2.4 Hz), 7.76 (s, 1H), 7.43 (m, 2H), 7.40 (s, 1H), 7.32 (m, 4H), 7.28 (m, 1H), 6.61(d, 1H, J=5.5 Hz), 3.89 (s, 3H), 3.74 (s, 2H). MS (m/z): 502.4 (M+H) (found).

Provenance & Evidence