2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631335, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.024 g, 0.049 mmol), 2,5-dimorpholinopyridin-3-amine (0.098 g, 0.37 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(pyrazin-2-yl)quinoline (0.090 g, 0.31 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.074 g, 0.77 mmol) in toluene (3.1 mL) at 120° C. for 5 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyrazin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 9.25 (1H, d, J=1.6 Hz), 8.67 (2H, m), 7.81 (1H, d, J=11.7 Hz), 7.65 (1H, d, J=2.7 Hz), 7.63 (1H, m), 7.02-7.10 (1H, ddd, J=13.5, 8.6, 2.5 Hz), 6.42 (1H, d, J=2.3 Hz), 3.92 (4H, br. s.), 3.81 (4H, app t, J=4.3 Hz), 3.25 (4H, br. s), 3.07 (4H, app t, J=4.3 Hz), 2.25 (3H, s). Mass Spectrum (ESI) m/e=520.2 (M+1).

Provenance & Evidence