2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631323, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.023 g, 0.047 mmol), 2,5-dimorpholinopyridin-3-amine (0.094 g, 0.35 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(2-methylpyridin-4-yl)quinoline (0.090 g, 0.30 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.071 g, 0.74 mmol) in toluene (2.7 mL) at 120° C. for 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-3-methyl-2-(2-methylpyridin-4-yl)quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.67 (1H, dd, J=4.9, 0.6 Hz), 7.71 (1H, d, J=11.0 Hz), 7.67 (1H, d, J=2.5 Hz), 7.62 (1H, ddd, J=9.4, 2.5, 1.4 Hz), 7.39 (1H, br s), 7.28 (1H, br s), 7.04 (1H, ddd, J=13.4, 8.6, 2.5 Hz), 6.33 (1H, dd, J=2.3, 0.4 Hz), 3.91 (4H, t, J=4.7 Hz), 3.83 (4H, app t, J=4.7 Hz), 3.20 (4H, br. s), 3.03 (4H, app t, J=4.9 Hz), 2.69 (3H, s), 2.13 (3H, s). Mass Spectrum (ESI) m/e=533.2 (M+1).

Provenance & Evidence