2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 67507807, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.024 g, 0.050 mmol), 5-morpholinopyridin-3-amine (0.067 g, 0.37 mmol), 4-chloro-5,7-difluoro-2-(2-methoxypyridin-4-yl)-3-methylquinoline (0.1 g, 0.31 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.075 g, 0.78 mmol) in toluene (3.1 mL) at 100° C. for 46.5 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 5,7-difluoro-2-(2-methoxypyridin-4-yl)-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.50 (1H, d, J=1.6 Hz), 8.30-8.34 (1H, dd, J=5.1, 0.6 Hz), 7.80 (1H, d, J=2.3 Hz), 7.64 (1H, m), 7.58 (1H, d, J=2.3 Hz), 7.43-7.51 (1H, m), 7.21 (1H, dd, J=5.2, 1.5 Hz), 7.03 (1H, s), 6.59 (1H, t, J=2.3 Hz), 3.92 (3H, s), 3.70 (4H, m), 3.08 (4H, m), 2.08 (3H, s). Mass Spectrum (ESI) m/e=464.1 (M+1).

Provenance & Evidence