2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 50906990, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of X-Phos (0.024 g, 0.050 mmol), 2,5-dimorpholinopyridin-3-amine (0.099 g, 0.38 mmol), 4,6-dichloro-7-methoxy-3-methyl-2-(pyridin-2-yl)-quinoline (0.10 g, 0.31 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.011 g, 0.013 mmol) in toluene (3.13 mL) was added sodium t-butoxide (0.075 g, 0.78 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 (10 mL). The organic layers were combined and washed with brine (20 mL) and dried over magnesium sulfate. The crude product was purified by column chromatography on basic alumina (0 to 50% EtOAc) to give the desired product 6-chloro-N-(2,5-di-4-morpholinyl-3-pyridinyl)-7-methoxy-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.72-8.79 (1H, m), 7.80-7.96 (3H, m), 7.63 (2H, br s), 7.37-7.45 (1H, m), 7.27 (1H, m), 6.79 (1H, br. s.), 6.27 (1H, m), 4.06 (3H, s), 3.93 (4H, t, J=4.6 Hz), 3.71-3.81 (4H, m), 3.24 (4H, br. s.), 2.92-3.00 (4H, m), 2.35 (3H, s). Mass Spectrum (ESI) m/e=547.2 (M+1).

Provenance & Evidence