2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 8-chloro-N-(2,5-dimorpholinopyridin-3-yl)-3-methyl-2-(pyridin-2-yl)quinolin-4-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.026 g, 0.055 mmol), 2,5-dimorpholinopyridin-3-amine (0.110 g, 0.415 mmol), 4,8-dichloro-3-methyl-2-(pyridin-2-yl)quinoline (0.10 g, 0.35 mmol) and Pd2dba3 (0.013 g, 0.014 mmol) in toluene (3.46 mL) was added sodium t-butoxide (0.083 g, 0.865 mmol). The reaction mixture was heated to 120° C. and stirred for 45 min. After which the reaction was cooled to rt and diluted with water (25 mL). The mixture was extracted with EtOAc (3×10 mL) and DCM (1×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on basic alumina (0 to 50% EtOAc/hexane) to give the desired product 8-chloro-N-(2,5-di-4-morpholinyl-3-pyridinyl)-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.71 (1H, d, J=4.3 Hz), 8.15 (1H, d, J=7.8 Hz), 7.93 (1H, m), 7.82 (1H, d, J=7.4 Hz), 7.76 (1H, br. s.), 7.60 (1H, d, J=2.5 Hz), 7.34-7.47 (2H, m), 6.79 (1H, br. s.), 6.21 (1H, br. s.), 3.93 (4H, br. s.), 3.67-3.79 (4H, m), 3.25 (4H, br. s.), 2.93 (4H, br. s.), 2.49 (3H, s). Mass Spectrum (ESI) m/e=517.2 (M+1).

Provenance & Evidence