2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631285, 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-(6-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 (2.7 mL) at 120° C. for 7 days. 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-(6-methylpyridin-3-yl)-quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (1H, d, J=2.0 Hz), 7.90 (1H, dd, J=8.0, 2.3 Hz), 7.75 (1H, d, J=11.2 Hz), 7.66 (1H, J=2.7 Hz), 7.61 (1H, br d, J=9.2 Hz), 7.36 (4H, d, J=8.0 Hz), 6.98-7.06 (1H, ddd, J=13.3, 8.4, 2.4 Hz), 6.36 (1H, d, J=2.5 Hz), 3.91 (4H, t, J=4.8 Hz), 3.81 (4H, app t, J=4.37 Hz), 3.22 (4H, br. s.), 3.03 (3H, app t, J=4.9 Hz), 2.68 (3H, s), 2.18 (3H, s). Mass Spectrum (ESI) m/e=533.2 (M+1).

Provenance & Evidence