2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631272, 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-(4-methylpyridin-3-yl)quinoline (0.1 g, 0.33 mmol), Pd2dba3 (0.012 g, 0.013 mmol) and sodium tert-butoxide (0.079 g, 0.82 mmol) in toluene (3.3 mL) at 120° C. for 19 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-(4-methylpyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.54 (1H, d, J=5.1 Hz), 8.48 (1H, br. s), 7.78 (1H, d, J=5.7 Hz), 7.65 (1H, m), 7.55 (1H, d, J=2.5 Hz), 7.51 (1H, ddd, J=13.3, 9.2, 2.5 Hz), 7.41 (1H, d, J=5.1 Hz), 6.34 (1H, s), 3.74 (1H, br. s), 3.65 (4H, app t, J=4.3 Hz), br. s.), 3.19 (2H, br. s), 2.96 (4H, app t, J=5.0 Hz), 2.2 (2H, br. s), 2.15 (3H, s), 1.87 (3H, s). Mass Spectrum (ESI) m/e=533.2 (M+1).

Provenance & Evidence