2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631303, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.021 g, 0.044 mmol), 2,5-dimorpholinopyridin-3-amine (0.088 g, 0.33 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(2-(pyrrolidin-1-yl)pyridin-4-yl)quinoline (0.1 g, 0.28 mmol) and Pd2dba3 (0.010 g, 0.011 mmol) and sodium tert-butoxide (0.067 g, 0.70 mmol) in toluene (2.8 mL) at 100° C. for 1.0 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-(2-(pyrrolidin-1-yl)pyridin-4-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (1H, dd, J=2.3, 0.6 Hz), 7.84 (1H, dd, J=8.8, 2.5 Hz), 7.73 (1H, d, J=5.5 Hz), 7.59 (1H, dd, J=9.9, 1.7 Hz), 7.55 (1H, d, J=2.7 Hz), 7.35-7.43 (1H, m), 6.58 (1H, d, J=8.6 Hz), 6.39 (1H, d, J=2.5 Hz), 3.59-3.81 (8H, m), 3.47 (4H, t, J=6.5 Hz), 3.15 (2H, br. s.), 2.94-3.05 (4H, m), 2.83 (2H, br. s.), 2.13 (3H, s), 1.93-2.04 (4H, m). Mass Spectrum (ESI) m/e=588.2 (M+1).

Provenance & Evidence