The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.021 g, 0.044 mmol), 2,5-dimorpholinopyridin-3-amine (0.088 g, 0.33 mmol), 4-chloro-2-(4-chloropyridin-2-yl)-5,7-difluoro-3-methylquinoline (0.090 g, 0.28 mmol), Pd2dba3 (10.14 mg, 0.011 mmol) and sodium tert-butoxide (0.067 g, 0.69 mmol) in toluene (2.8 mL) at 120° C. for 28 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product 2-(4-chloropyridin-2-yl)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methylquinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.59 (1H, d, J=5.3 Hz), 7.98 (1H, d, J=0.6 Hz), 7.78 (1H, br. d, J=11.9 Hz), 7.64 (1H, d, J=2.5 Hz), 7.62 (1H, m), 7.40 (1H, dd, J=5.4, 2.1 Hz), 7.03 (2H, ddd, J=13.3, 8.61, 2.4 Hz), 6.44 (1H, br s), 3.93 (4H, br. s.), 3.82 (4H, app t, J=4.8 Hz), 3.25 (4H, br. s), 3.08 (4H, app t., J=4.8 Hz), 2.22 (3H, s). Mass Spectrum (ESI) m/e=553.2 (M+1).
