The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.025 g, 0.052 mmol), 2,5-dimorpholinopyridin-3-amine (0.103 g, 0.39 mmol), 4,8-dichloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.1 g, 0.33 mmol), Pd2dba3 (0.012 g, 0.013 mmol) and sodium tert-butoxide (0.078 g, 0.812 mmol) in toluene (3.3 mL) at 120° C. for 3 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product 8-chloro-N-(2,5-dimorpholinopyridin-3-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.72 (1H, d, J=1.6 Hz), 8.14 (1H, d, J=7.8 Hz), 7.94 (1H, td, J=7.7, 1.8 Hz), 7.75 (1H, br s.), 7.61 (1H, d, J=0.4 Hz), 7.42-7.39 (1H, m), 7.36 (1H, t, J=8.6 Hz), 6.80 (1H, br s.), 6.19 (1H, br. s.), 3.93 (4H, br s.), 3.74 (4H, m), 3.25 (4H, br. s.), 2.92 (4H, br. m.), 2.47 (3H, s). Mass Spectrum (ESI) m/e=535.2 (M+1).
