2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631491, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.026 g, 0.055 mmol), 2,5-dimorpholinopyridin-3-amine (0.109 g, 0.41 mmol), 4-chloro-6,8-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.1 g, 0.34 mmol), Pd2dba3 (0.013 g, 0.014 mmol) and sodium tert-butoxide (0.083 g, 0.86 mmol) in toluene (3.4 mL) at 120° C. for 3 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)-6,8-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, CDCl3-d) δ ppm 8.73 (1H, dd, J=1.6, 1.2 Hz), 7.89-8.00 (2H, m), 7.62 (1H, d, J=2.5 Hz), 7.40 (1H, ddd, J=7.4, 4.9, 1.4 Hz), 7.21-7.26 (2H, m), 6.70 (1H, br. s.), 6.19 (1H, m), 3.95-3.93 (4H, br. s.), 3.77-3.75 (4H, br. s.), 3.25 (4H, br s), 2.9-2.95 (4H, m), 2.44 (3H, s). Mass Spectrum (ESI) m/e=519.2 (M+1).

Provenance & Evidence