Cesium carbonate → N-(4-((2-(3,3-dimethylureido)pyridin-4-yl)oxy)-2,5-difluorophenyl)-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 (0.100 g, 0.194 mmol), N,N-dimethylurea (0.102 g, 1.163 mmol), Cs2CO3 (0.158 g, 0.485 mmol), Xantphos (0.034 g, 0.058 mmol), Pd2(dba)3 (0.023 g, 0.025 mmol), and dioxane (5 mL) were combined to afford N-(4-((2-(3,3-dimethylureido)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (40 mg, 36.4% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.19 (s, 1 H), 8.92 (s, 1 H), 8.31 (dd, J=12.6, 7.2 Hz, 1 H), 8.10 (d, J=5.7 Hz, 1 H), 7.92 (d, J=7.8 Hz, 1 H), 7.52-7.46 (m, 3 H), 7.41-7.33 (m, 3 H), 6.62 (dd, J=5.7, 2.4 Hz, 1 H), 6.55 (d, J=7.9 Hz, 1 H), 4.28 (q, J=7.0 Hz, 2 H), 2.87 (s, 6 H), 1.33 (t, J=7.0 Hz, 3 H); MS (ESI) m/z: 568.2 (M+H+).

Provenance & Evidence