2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 50907190, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.023 g, 0.048 mmol), 2,5-dimorpholinoaniline (0.095 g, 0.36 mmol), 4-chloro-3-methyl-2,8-di(pyridin-2-yl)quinoline (0.1 g, 0.30 mmol) and Pd2dba3 (0.011 g, 0.012 mmol) in toluene (3.00 mL) was added sodium tert-butoxide (0.072 g, 0.753 mmol). The reaction mixture was heated to 120° C. and stirred for 45 min. The reaction was then cooled to rt and diluted with water (25 mL). The mixture was extracted with EtOAc (2×10 mL) and DCM (1×10 mL). The organic layers were combined and washed with brine (1×20 mL) and dried over magnesium sulfate. The crude product was purified by column chromatography on basic alumina (0 to 50% EtOAc in hexane) to give the desired product N-(2,5-di(4-morpholinyl)phenyl)-3-methyl-2,8-di(2-pyridinyl)-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.78 (1H, d, J=4.1 Hz), 8.69 (1H, m), 8.30 (1H, m), 8.20 (1H, m), 7.96 (2H, m), 7.80 (2H, m), 7.59 (1H, dd, J=8.3, 7.3 Hz), 7.32 (2H, m), 7.10 (1H, m), 6.43 (1H, m), 6.03 (1H, br. s), 3.92 (4H, br. s), 3.71 (4H, br. s), 3.08 (4H, br. s), 2.91 (4H, br. s), 2.53 (3H, s). Mass Spectrum (ESI) m/e=559.3 (M+1).

Provenance & Evidence