2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 8-chloro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(pyridin-2-yl)quinolin-4-amine

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.026 g, 0.055 mmol), 5-morpholinopyridin-3-amine (0.074 g, 0.42 mmol), 4,8-dichloro-3-methyl-2-(pyridin-2-yl)quinoline (0.1 g, 0.35 mmol) and Pd2dba3 (0.013 g, 0.014 mmol) and sodium tert-butoxide (0.083 g, 0.87 mmol) in toluene (3.5 mL) at 100° C. for 1.1 h. The crude product was purified by column chromatography on silica gel (0 to 100% DCM/MeOH/ammonium hydroxide (90/9/1)) to give the desired product 8-chloro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(pyridin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.69-8.73 (2H, m), 7.95-8.06 (3H, m), 7.92 (1H, dd, J=7.4, 1.2 Hz), 7.81 (1H, d, J=2.3 Hz), 7.50-7.56 (3H, m), 6.56 (1H, t, J=2.4 Hz), 3.70 (4H, m), 3.06 (4H, m), 2.25 (3H, s). Mass Spectrum (ESI) m/e=432.1 (M+1).

Provenance & Evidence