Potassium Carbonate → HCID 11963306, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-N-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-2-oxo-1-phenyl-1,2-dihydro-pyridine-3-carboxamide (0.075 g, 0.13 mmol) was suspended in DMF (1.5 mL) and then was added a solution of potassium carbonate (0.053 g, 0.38 mmol) in water (0.5 mL), phenylboronic acid (0.015 g, 0.13 mmol) and PdCl2(dppf)2 (0.0093 g, 0.013 mmol). The reaction mixture was heated at 80° C. for 6 hours. The reaction mixture was diluted with ethyl acetate and water then extracted with ethyl acetate. The organic layer was washed with brine then dried over sodium sulfate and concentrated under vacuum. The remaining residue was purified by silica gel chromatography (1% methanol/dichloromethane to 2% methanol/dichloromethane) to give N-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-2-oxo-1,5-diphenyl-1,2-dihydropyridine-3-carboxamide as a light yellow solid (0.069 g, 0.12 mmol, 92% yield). MS (ESI pos. ion) m/z: 588 (MH+). Calc'd exact mass for C35H26FN3O5: 587. 1H NMR (400 MHz, DMSO-d6) 12.19 (s, 1 H), 8.87 (d, J=2.91 Hz, 1 H), 8.40-8.55 (m, 2 H), 8.09 (dd, J=12.82, 2.34 Hz, 1 H), 7.75 (d, J=7.33 Hz, 2 H), 7.16-7.67 (m, 12 H), 6.49 (d, J=5.05 Hz, 1 H), 3.95 (s, 6 H).

Provenance & Evidence