2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631066, 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, 0.050 mmol), 2,5-dimorpholinopyridin-3-amine (0.099 g, 0.37 mmol), 4-chloro-5,7-difluoro-2-(2-methoxypyridin-4-yl)-3-methylquinoline (0.1 g, 0.31 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.075 g, 0.78 mmol) in toluene (3.1 mL) at 120° C. for 3.2 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-2-(2-methoxypyridin-4-yl)-3-methylquinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.33 (1H, dd, J=5.2, 0.7 Hz), 7.72 (1H, d, J=11.0 Hz), 7.66 (1H, d, J=2.7 Hz), 7.60 (1H, m), 7.07-7.01 (2H, m), 6.91 (1H, s), 6.32 (1H, d, J=2.3 Hz), 4.02 (3H, s), 3.91 (4H, t, J=4.7 Hz), 3.83 (4H, app t, J=4.7 Hz), 3.25 (4H, br. s), 3.03 (4H, app t, J=4.9 Hz), 2.13 (3H, s). Mass Spectrum (ESI) m/e=549.3 (M+1).

Provenance & Evidence