2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 50906787, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.019 g, 0.040 mmol), 2,5-dimorpholinopyridin-3-amine (0.078 g, 0.30 mmol), 4-chloro-3-methyl-2,8-di(pyridin-2-yl)quinoline (0.082 g, 0.25 mmol) and Pd2dba3 (9.05 mg, 9.89 μmol) in toluene (2.5 mL) was added sodium t-butoxide (0.059 g, 0.62 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 (10 mL). The mixture was extracted with EtOAc (3×10 mL) and DCM (10 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on basic alumina (0 to 100% EtOAc/DCM) to give the desired product N-(2,5-di-4-morpholinyl-3-pyridinyl)-3-methyl-2,8-di-2-pyridinyl-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.75-8.84 (1H, m), 8.69 (1H, br m), 8.28 (1H, d, J=7.6 Hz), 8.21 (1H, d, J=7.6 Hz), 7.97 (1H, d, J=7.6 Hz), 7.84 (2H, br. m.), 7.78 (1 h, m), 7.62 (2H, dd, J=16.0, 7.8 Hz), 7.28-7.35 (2H, br. m.), 6.82 (1H, br. s.), 6.25 (1H, br. s.), 3.95 (4H, br. s.), 3.73 (4H, br. s.), 3.27 (4H, br. s.), 2.93 (4H, br. s.), 2.52 (3H, s). Mass Spectrum (ESI) m/e=560.2 (M+1).

Provenance & Evidence