2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631390, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.016 g, 0.033 mmol), 2,5-dimorpholinopyridin-3-amine (0.065 g, 0.25 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)quinoline (0.08 g, 0.21 mmol), Pd2dba3 (0.008 g, 0.008 mmol) and sodium tert-butoxide (0.049 g, 0.51 mmol) in toluene (2.1 mL) at 100° C. for 2 h. The crude product was purified by column chromatography on silica gel (0 to 100% DCM/methanol/ammonium hydroxide (90/9/1)) to give the desired product N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.50 (1H, d, J=2.3 Hz), 7.96 (1H, dd, J=9.2, 2.5 Hz), 7.83 (1H, d, J=2.7 Hz), 7.69 (2H, m), 7.21 (2H, m), 4.61 (2H, br. d), 3.73 (4H, m), 3.57 (3H, br. d.), 3.46 (4H, br. s.), 3.29 (3H, m), 3.15-3.06 (7H, m), 2.88 (4H, s), 2.04 (3H, s). Mass Spectrum (ESI) m/e=617.3 (M+1).

Provenance & Evidence