2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 67508005, 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, 0.048 mmol), 2,5-dimorpholinopyridin-3-amine (0.095 g, 0.36 mmol), 4-chloro-2-(6-ethoxypyridin-3-yl)-5,7-difluoro-3-methylquinoline (0.1 g, 0.30 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.045 g, 0.47 mmol) in toluene (3.0 mL) at 100° C. for 2 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)-2-(6-ethoxypyridin-3-yl)-5,7-difluoro-3-methylquinolin-4-amine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.46 (1H, d, J=2.0 Hz), 8.01 (1H, dd, J=8.6, 2.4 Hz), 7.79 (1H, d, J=5.6 Hz), 7.65 (1H, dd, J=9.8, 1.7 Hz), 7.56 (1H, d, J=2.4 Hz), 7.47 (1H, ddd, J=13.1, 9.4, 2.4 Hz), 6.96 (1H, d, J=8.6 Hz), 6.44 (1H, d, J=2.7 Hz), 4.40 (2H, q, J=6.9 Hz), 3.58-3.83 (9H, m), 3.16 (2H, br. s.), 2.94-3.06 (5H, m), 2.84 (2H, br. s.), 2.11 (3H, s), 1.37 (3H, t, J=7.1 Hz). Mass Spectrum (ESI) m/e=563.3 (M+1).

Provenance & Evidence