The Buchwald coupled product was prepared according to Procedure S using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.020 g, 0.043 mmol), 2,5-dimorpholinopyridin-3-amine (0.084 g, 0.32 mmol), 4-(5-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2-yl)morpholine (0.1 g, 0.27 mmol), Pd2dba3 (0.010 g, 0.011 mmol) and sodium tert-butoxide (0.079 g, 0.82 mmol) in toluene (2.7 mL) at 120° C. for 1.9 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(6-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (1H, dd, J=2.4, 0.7 Hz), 7.90 (1H, dd, J=8.8, 2.5 Hz), 7.75 (1H, d, J=5.9 Hz), 7.60 (1H, ddd, J=10.0, 2.5, 1.0 Hz), 7.55 (1H, d, J=2.5 Hz), 7.42 (1H, dd, J=4.0, 2.6 Hz), 6.98 (1H, d, J=8.6 Hz), 6.41 (1H, d, J=2.5 Hz), 3.69-3.78 (6H, m), 3.61-3.69 (6H, m), 3.52-3.61 (4H, m), 3.14 (2H, br. s.), 2.95-3.05 (4H, m), 2.83 (2H, br. s.), 2.12 (3H, s). Mass Spectrum (ESI) m/e=604.3 (M+1).
