2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 67508113, compound

Participants

Reaction Steps

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.024 g, 0.050 mmol), 2,5-dimorpholinopyridin-3-amine (0.099 g, 0.37 mmol), 4-chloro-5,7-difluoro-2-(2-methoxypyridin-3-yl)-3-methylquinoline (0.10 g, 0.312 mmol) and Pd2dba3 (0.011 g, 0.012 mmol) in toluene (3.12 mL) was added sodium t-butoxide (0.075 g, 0.78 mmol). The reaction mixture was heated to 120C. and stirring continued for 2 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-2-(2-methoxy-3-pyridinyl)-3-methyl-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.33 (1H, dd, J=4.9, 1.8 Hz), 7.76 (1H, m), 7.64 (2H, br. s.), 7.11 (1H, dd, J=7.2, 5.1 Hz), 7.00 (1H, m), 6.39 (1H, br. s.), 3.96 (3H, s), 3.92 (4H, br s), 3.78-3.86 (4H, m), 3.39 (2H, br. s.), 3.06 (6H, br. s.), 2.00 (3H, s). Mass Spectrum (ESI) m/e=549.3 (M+1).

Provenance & Evidence