2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631096, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.020 g, 0.041 mmol), 2,5-dimorpholinopyridin-3-amine (0.082 g, 0.31 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)quinoline (0.10 g, 0.26 mmol) and Pd2dba3 (0.009 g, 0.010 mmol) and sodium tert-butoxide (0.072 g, 0.75 mmol) in toluene (2.6 mL) at 100° C. for 1.6 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-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.25 (1H, d, J=5.5 Hz), 7.80 (1H, d, J=6.3 Hz), 7.62-7.67 (1H, m), 7.55 (1H, d, J=2.5 Hz), 7.49 (1H, ddd, J=13.2, 9.2, 2.6 Hz), 6.93 (1H, s), 6.81 (1H, dd, J=5.0, 1.1 Hz), 6.44 (1H, d, J=2.7 Hz), 3.79-3.61 (8H, m), 3.48-3.56 (4H, m), 3.14 (2H, br. s.), 2.99 (4H, d, J=2.2 Hz), 2.83 (2H, br. s.), 2.36-2.44 (4H, m), 2.22 (3H, s), 1.99 (3H, s). Mass Spectrum (ESI) m/e=617.3 (M+1).

Provenance & Evidence