2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631533, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.021 g, 0.044 mmol), 2,5-dimorpholinopyridin-3-amine (0.086 g, 0.33 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(4-phenylpyridin-2-yl)quinoline (0.1 g, 0.27 mmol), Pd2dba3 (0.010 g, 0.011 mmol) and sodium tert-butoxide (0.066 g, 0.68 mmol) in toluene (2.7 mL) at 120° C. for 3.25 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(4-phenylpyridin-2-yl)-quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.75 (1H, d, J=5.1 Hz), 8.10 (1H, s), 7.76 (3H, m), 7.64-7.61 (3H, m), 7.57-7.49 (3H, m), 7.03 (1H, ddd, J=13.5, 8.4, 2.5 Hz), 6.48 (1H, br. s.), 3.93 (4H, app t, J=4.8 Hz), 3.81 (4H, app t, J=4.5 Hz), 3.25 (4H, br. s), 3.09 (11H, app t, J=4.9 Hz), 2.25 (3H, s). Mass Spectrum (ESI) m/e=595.3 (M+1).

Provenance & Evidence