The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.019 g, 0.040 mmol), 2,5-dimorpholinopyridin-3-amine (0.080 g, 0.30 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(4-vinylpyridin-2-yl)quinoline (0.08 g, 0.25 mmol), Pd2dba3 (0.009 g, 0.010 mmol) and sodium tert-butoxide (0.061 g, 0.63 mmol) in toluene (2.5 mL) at 100° C. for 4.5 h. The crude product was purified by column chromatography on silica gel (0 to 100% DCM/MeOH/ammonium hydroxide (90/9/1)) to give the desired product N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(4-vinylpyridin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.54 (1H, br. s), 8.28 (1H, d, J=5.9 Hz), 7.83 (1H, d, J=2.7 Hz), 7.50-7.58 (2H, m), 7.28 (1H, d, J=2.7 Hz), 7.24 (1H, m), 7.08 (1H, d, J=2.2 Hz), 6.87 (1H, dd, J=5.7, 2.3 Hz), 5.76 (1H, m), 5.41 (1H, dd, 17.8, 1.6 Hz), 3.71-3.76 (4H, m), 3.55-3.60 (4H, m), 3.08 (4H, m), 3.02 (4H, m), 2.40 (3H, s). Mass Spectrum (ESI) m/e=545.2 (M+1).
