2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631459, 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, 0.052 mmol), 2,5-dimorpholinopyridin-3-amine (0.103 g, 0.39 mmol), 4-chloro-5,7-difluoro-2-(6-fluoropyridin-3-yl)-3-methylquinoline (0.1 g, 0.32 mmol), Pd2dba3 (0.012 g, 0.013 mmol) and sodium tert-butoxide (0.078 g, 0.81 mmol) in toluene (3.2 mL) at 100° C. for 2.1 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-2-(6-fluoropyridin-3-yl)-3-methylquinolin-4-amine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.52 (1H, d, J=2.4 Hz), 8.27 (1H, td, J=8.2, 2.4 Hz), 7.82 (1H, d, J=5.9 Hz), 7.67 (1H, d, J=10.0 Hz), 7.56 (1H, d, J=2.7 Hz), 7.47-7.53 (1H, m), 7.38 (1H, dd, J=8.4, 2.6 Hz), 6.47 (1H, d, J=2.7 Hz), 3.61-3.77 (8H, m), 3.15 (2H, br. s.), 2.96-3.05 (4H, m), 2.83 (2H, br. s.), 2.06 (3H, s). Mass Spectrum (ESI) m/e=563.3 (M+1).

Provenance & Evidence