Methanol → 2-(2-Fluorophenyl)-3-methyl-N-(2-(4-morpholinyl)-5-(4-pyridinyl)phenyl)-4-quinolinamine

Participants

Reaction Conditions

Reaction Steps

A mixture of sodium carbonate (68 mg, 640 μmol), pyridin-4-ylboronic acid (40 mg, 329 μmol), N-(5-bromo-2-morpholinophenyl)-2-(2-fluorophenyl)-3-methylquinolin-4-amine (90 mg, 183 μmol) and dichlorobis(triphenylphosphine)-palladium(II) (13 mg, 18 μmol) in water (2.00 mL) and 1,4-dioxane (8.00 mL) was purged with nitrogen then heated in a microwave vessel with stirring at 130° C. for 60 min, after which time LC-MS indicated no starting material remained and desired product predominated. The reaction was diluted with 30 mL water and extracted with 3×15 mL EtOAc. The combined organic extracts were stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a dark brown oil. The desired product was isolated as a colorless solid by chromatography on silica gel eluting with a gradient of 1-5% MeOH in DCM. 1H NMR (400 MHz, chloroform-d) δ ppm 8.55 (2H, dd, J=4.3, 1.6 Hz), 8.21 (1H, d, J=8.2 Hz), 7.93 (1H, d, J=8.6 Hz), 7.61-7.79 (3H, m), 7.40-7.61 (3H, m), 7.10-7.40 (7H, m), 6.74 (1H, d, J=0.8 Hz), 3.98 (4H, t, J=4.5 Hz), 3.02-3.29 (4H, m), 2.26 (3H, d, J=2.3 Hz). Mass Spectrum (ESI) m/e=491.2 (M+1).

Provenance & Evidence