Cesium carbonate → N-(2,5-difluoro-4-((2-isobutyramidopyridin-4-yl)oxy)phenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Participants

Reaction Steps

Using the procedure of Example 4, N-(4-((2-chloropyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.15 g, 0.29 mmol), isobutyramide (0.10 g, 1.16 mmol), Xantphos (0.02 g, 0.032 mmol), and Cs2CO3 (0.14 g, 0.44 mmol), Pd2(dba)3 (0.015 g, 0.015 mmol), and dioxane (5 mL) were combined to obtain N-(2,5-difluoro-4-((2-isobutyramidopyridin-4-yl)oxy)phenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (55 mg, 35% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.23 (s, 1H), 10.52 (s, 1H), 8.34-8.33 (m, 1H), 8.19 (d, J=5.7 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.69 (d, J=2.4 Hz, 1H), 7.50-7.49 (m, 3H), 7.36 (t, J=8.7 Hz, 2H), 6.74 (dd, J=5.7, 2.5 Hz, 1H), 6.55 (d, J=7.9 Hz, 1H), 4.28 (q, J=7.0 Hz, 2H), 2.69 (m, 1H), 1.34 (t, J=7.0 Hz, 3H), 1.02 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 581.2 (M+H+).

Provenance & Evidence