Ethyl Acetate → 2-(2-Fluorophenyl)-3-methyl-N-(2-(4-morpholinyl)-5-(3-thiophenyl)phenyl)-4-quinolinamine

Participants

Reaction Conditions

Reaction Steps

A mixture of dichlorobis(triphenylphosphine)palladium(II) (13 mg, 18 μmol), N-(5-bromo-2-morpholinophenyl)-2-(2-fluorophenyl)-3-methylquinolin-4-amine (88 mg, 179 μmol), thiophen-3-ylboronic acid (34 mg, 268 μmol) and sodium carbonate (57 mg, 536 μmol) in water (0.25 mL) and 1,4-dioxane (1.00 mL) was purged with nitrogen then heated in a microwave vessel to 130° C. for 60 min, after which time TLC indicated no starting material remained and LC-MS indicated only desired product present. The reaction was partitioned between water and EtOAc (30 mL ea). The organic separation was stirred over anhydrous magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a brown film. The desired product was isolated by chromatography on silica gel eluting isocratically with 33% EtOAc in hexane to afford a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.99 (2H, dd, J=15.3, 8.2 Hz), 7.79 (1H, s), 7.71 (1H, dd, J=7.0, 7.0 Hz), 7.45-7.63 (5H, m), 7.32-7.45 (2H, m), 7.12-7.29 (3H, m), 6.69 (1H, d, J=1.6 Hz), 3.59 (4H, br. s.), 2.91 (4H, br. s.), 2.06 (3H, d, J=1.6 Hz). Mass Spectrum (ESI) m/e=496.1 (M+1).

Provenance & Evidence