2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631579, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.022 g, 0.046 mmol), 2,5-dimorpholinopyridin-3-amine (0.092 g, 0.35 mmol), 2-(4-tert-butylphenyl)-4-chloro-5,7-difluoro-3-methylquinoline (0.1 g, 0.29 mmol) and Pd2dba3 (10.6 mg, 0.012 mmol) in toluene (2.89 mL) was added sodium t-butoxide (0.069 g, 0.72 mmol). The reaction mixture was heated to 120° C. and stirring continued for 1.5 h. The reaction was cooled to rt and diluted with water (15 mL). The mixture was extracted with EtOAc (2×15 mL) and DCM (1×15 mL). The organic layers were combined and washed with brine (1×20 mL) and dried over magnesium sulfate. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product N-(2,5-di(4-morpholinyl)-3-pyridinyl)-5,7-difluoro-3-methyl-2-(4-(2-methyl-2-propanyl)phenyl)-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 7.59-7.73 (3H, m), 7.50-7.57 (4H, m), 6.98 (1H, m), 6.37 (1H, br. s.), 3.92 (4H, br. s.), 3.79-3.87 (4H, m), 3.25 (4H, br. s.), 2.99-3.09 (4H, m), 2.18 (3H, s), 1.36-1.45 (9H, s). Mass Spectrum (ESI) m/e=574.3 (M+1).

Provenance & Evidence