The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.020 g, 0.042 mmol), 2,5-dimorpholinopyridin-3-amine (0.083 g, 0.32 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(1-methyl-1H-indazol-4-yl)quinoline (0.090 g, 0.26 mmol), Pd2dba3 (9.6 mg, 10.50 μmol) and sodium tert-butoxide (0.063 g, 0.66 mmol) in toluene (2.6 mL) at 120° C. for 3.3 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-(1-methyl-1H-indazol-4-yl)quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (1H, s), 7.80 (1H, br m), 7.65 (1H, d, J=2.5 Hz), 7.63 (1H, br. s.), 7.53 (4H, s), 7.54 (2H, m), 7.25 (1H, m), 7.05 (1H, ddd, J=13.4, 8.5, 2.7 Hz), 6.41 (1H, br. s.), 4.16 (3H, s), 3.92 (4H, app t, J=4.8 Hz), 3.85 (4H, app dd, J=5.7, 3.9 Hz), 3.25 (4H, br s.), 3.08 (11H, app dd, J=4.3, 2.3 Hz), 2.06 (3H, s). Mass Spectrum (ESI) m/e=572.2 (M+1).
