2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631082, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.024 g, 0.050 mmol), 2,5-dimorpholinopyridin-3-amine (0.098 g, 0.37 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(6-(4-methylpiperidin-1-yl)pyridin-3-yl)quinoline (0.12 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 100° C. for 5 h. The crude product was purified by column chromatography on silica gel (0 to 100% DCM/methanol/ammonium hydroxide (90/9/1)) to give the desired product N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(6-(4-methylpiperidin-1-yl)pyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (1H, d, J=2.3 Hz), 7.84 (1H, dd, J=8.9, 2.4 Hz), 7.74 (1H, d, J=5.3 Hz), 7.59 (1H, dd, J=9.8, 1.8 Hz), 7.55 (1H, d, J=2.5 Hz), 7.35-7.45 (1H, m), 6.95 (1H, d, J=9.0 Hz), 6.40 (1H, d, J=2.5 Hz), 4.39 (2H, d, J=13.5 Hz), 3.59-3.80 (8H, m), 3.17 (4H, m), 2.94-3.04 (4H, m), 2.87 (4H, m), 2.13 (3H, s), 1.69 (3H, m), 1.14 (2H, m), 0.94 (3H, d, J=6.3 Hz). Mass Spectrum (ESI) m/e=616.3 (M+1).

Provenance & Evidence