2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → N-(3-chloro-5-morpholinophenyl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine

Participants

Reaction Steps

The Buchwald coupled products were prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.026 g, 0.055 mmol), 3-chloro-5-morpholinoaniline (0.088 g, 0.413 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.1 g, 0.344 mmol) and Pd2dba3 (0.013 g, 0.014 mmol) and sodium tert-butoxide (0.063 g, 0.66 mmol) in toluene (3.4 mL) at 100° C. for 45 mins. The crude product was purified by column chromatography on alumina (0 to 50% EtOAc in hexanes) to give the desired product N-(3-chloro-5-morpholinophenyl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.72 (1H, ddd, J=4.9, 1.8, 1.0 Hz), 7.89 (1H, td, J=7.4, 1.8 Hz), 7.80-7.85 (1H, m), 7.67 (1H, br. s.), 7.38 (1H, ddd, J=7.5, 4.8, 1.2 Hz), 7.02 (2H, ddd, J=13.7, 8.6, 2.5 Hz), 6.51 (1H, s), 6.36 (1H, s), 6.27 (1H, s), 3.83 (4H, app t, J=4.9 Hz), 3.15 (4H, app t, J=4.9 Hz), 2.17 (3H, s). Mass Spectrum (ESI) m/e=467.2 (M+1).

Provenance & Evidence