2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631224, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.025 g, 0.053 mmol), 2,5-dimorpholinopyridin-3-amine (0.104 g, 0.39 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(2-methylpyridin-3-yl)quinoline (0.1 g, 0.33 mmol), Pd2dba3 (0.012 g, 0.013 mmol) and sodium tert-butoxide (0.064 g, 0.67 mmol) in toluene (3.3 mL) at 100° C. for 43 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-(2-methylpyridin-3-yl)-quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.57 (1H, dd, J=4.9, 2.0 Hz)), 7.76 (1H, m), 7.72 (1H, m), 7.63 (1H, m), 7.55 (1H, d, J=2.5 Hz), 7.50 (1H, m), 7.38 (1H, dd, J=7.4, 4.7 Hz), 6.31 (1H, br. s.), 3.73 (4H, br. s), 3.65 (4H, app t, J=4.5 Hz), 3.17 (2H, br. s), 2.94 (4H, app t, J=4.5 Hz), 2.82 (2H, br. s), 2.29 (3H, s), 1.87 (3H, s). Mass Spectrum (ESI) m/e=533.2 (M+1).

Provenance & Evidence