2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631263, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.023 g, 0.049 mmol), 2,5-dimorpholinopyridin-3-amine (0.096 g, 0.37 mmol), 4-chloro-5,7-difluoro-2-(1H-indol-4-yl)-3-methylquinoline (0.1 g, 0.30 mmol) and Pd2dba3 (0.011 g, 0.012 mmol) in toluene (3.04 mL) was added sodium t-butoxide (0.073 g, 0.760 mmol). The reaction mixture was heated to 120° C. and stirring continued for 7 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-(1H-indol-4-yl)-3-methyl-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.41 (1H, br. s.), 7.81 (1H, br. s), 7.66 (2H, br. s.), 7.51 (1H, m), 7.32 (1H, br. s), 7.19-7.26 (2H, m), 7.05 (1H, br. s.), 6.44 (1H, br. s.), 6.31 (1H, br. s.), 3.92 (4H, br. s), 3.80-3.88 (4H, m), 3.27 (4H, br. s), 3.02-3.14 (4H, m), 2.02 (3H, s). Mass Spectrum (ESI) m/e=557.2 (M+1).

Provenance & Evidence