2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631166, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.023 g, 0.049 mmol), 2,5-dimorpholinopyridin-3-amine (0.098 g, 0.37 mmol), 4-chloro-2-(5-chloropyridin-3-yl)-5,7-difluoro-3-methylquinoline (0.1 g, 0.31 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.074 g, 0.77 mmol) in toluene (3.1 mL) at 120° C. for 3.2 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product 2-(5-chloropyridin-3-yl)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methylquinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.71 (2H, dd, J=11.5, 2.2 Hz), 8.00 (1H, t, J=2.2 Hz), 7.79 (1H, d, J=11.0 Hz), 7.68 (1H, d, J=2.7 Hz), 7.61 (1H, d, J=9.4 Hz), 7.05 (1H, ddd, J=13.1, 8.4, 2.4 Hz.), 6.36 (1H, br. s.), 3.91 (4H, br. s.), 3.83 (4H, app t, J=4.7 Hz), 3.22 (4H, br. s), 3.05 (4H, app t, J=4.9 Hz), 2.18 (3H, s). Mass Spectrum (ESI) m/e=553.2 (M+1).

Provenance & Evidence