2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631442, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.020 g, 0.043 mmol), 5-morpholinopyridin-3-amine (0.057 g, 0.320 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(6-(piperazin-1-yl)pyridin-3-yl)quinoline (0.1 g, 0.27 mmol), Pd2dba3 (0.010 g, 0.011 mmol) and sodium tert-butoxide (0.049 g, 0.51 mmol) in toluene (2.7 mL) at 100° C. for 2.5 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(6-(piperazin-1-yl)pyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.45 (2H, dd, J=4.9, 2.2 Hz), 7.89 (1H, dd, J=8.9, 2.4 Hz), 7.79 (1H, d, J=2.5 Hz), 7.56-7.60 (2H, m), 7.35-7.41 (1H, m), 6.93 (1H, d, J=8.8 Hz), 6.55 (1H, t, J=2.3 Hz), 3.70 (4H, m), 3.55 (4H, m), 3.08 (4H, m), 2.85 (4H, m), 2.19 (3H, s). Mass Spectrum (ESI) m/e=518.2 (M+1).

Provenance & Evidence