2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 8-chloro-N-(5'-methoxy-5-morpholino-2,3'-bipyridin-3-yl)-3-methyl-2-(4-methylpyridin-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 (0.020 g, 0.042 mmol), 5′-methoxy-5-morpholino-2,3′-bipyridin-3-amine (0.091 g, 0.32 mmol), 4,8-dichloro-3-methyl-2-(4-methylpyridin-2-yl)quinoline (0.08 g, 0.26 mmol) and Pd2dba3 (0.010 g, 0.011 mmol) and sodium tert-butoxide (0.063 g, 0.66 mmol) in toluene (2.6 mL) at 100° C. for 48.3 h. The crude product was purified by column chromatography on alumina (0 to 50% EtOAc in hexanes) to give the desired product 8-chloro-N-(5′-methoxy-5-morpholino-2,3′-bipyridin-3-yl)-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.55 (1H, d, J=4.9 Hz), 8.35 (1H, s), 8.12 (2H, dd, J=4.6, 2.2 Hz), 7.89 (2H, dd, J=8.0, 2.3 Hz), 7.85 (1H, s), 7.66 (1H, s), 7.53 (1H, t, J=7.6 Hz), 7.34 (1H, m), 7.29 (1H, dd, J=2.7, 1.8 Hz), 5.70-5.72 (1H, m), 3.76 (3H, s), 3.60 (4H, t, J=4.8 Hz), 3.23 (4H, m), 2.46 (3H, s), 2.27 (3H, s). Mass Spectrum (ESI) m/e=553.3 (M+1).

Provenance & Evidence