2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631196, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.022 g, 0.045 mmol), 2,5-dimorpholinopyridin-3-amine (0.090 g, 0.34 mmol), 4-chloro-2-(2,3-dimethylphenyl)-5,7-difluoro-3-methylquinoline (0.090 g, 0.28 mmol), Pd2dba3 (0.010 g, 0.011 mmol) and sodium tert-butoxide (0.068 g, 0.71 mmol) in toluene (2.8 mL) at 120° C. for 1 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product 2-(2,3-dimethylphenyl)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methylquinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 7.71-7.68 (1H, br d, J=10.0 Hz), 7.63 (2H, m), 7.22-7.28 (2H, m), 6.98-7.11 (2H, m), 6.26 (1H, d, J=2.3 Hz), 3.93 (4H, m), 3.80 (4H, app t, J=4.2 Hz), 3.35 (4H, br. s), 3.01 (4H, app t, J=4.2 Hz), 2.37 (3H, s), 2.07 (3H, s), 1.94 (3H, s). Mass Spectrum (ESI) m/e=546.3 (M+1).

Provenance & Evidence