2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631372, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.021 g, 0.045 mmol), 2,5-dimorpholinopyridin-3-amine (0.088 g, 0.34 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(6-(trifluoromethyl)pyridin-3-yl)quinoline (0.1 g, 0.28 mmol), Pd2dba3 (0.010 g, 0.011 mmol) and sodium tert-butoxide (0.079 g, 0.82 mmol) in toluene (2.8 mL) at 120° C. for 43 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)-5,7-difluoro-3-methyl-2-(6-(trifluoromethyl)-pyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 (1H, d, J=1.8 Hz), 8.35 (1H, dd, J=7.8, 1.6 Hz), 8.11 (1H, d, J=8.0 Hz), 7.86 (1H, d, J=6.1 Hz), 7.69 (1H, m), 7.56 (1H, d, J=2.5 Hz), 7.53, (1H, ddd, J=12.9, 9.0, 2.5 Hz), 6.51 (1H, d, J=2.5 Hz), 3.67 (8H, m), 3.17 (2H, br. s), 3.02 (4H, m), 2.85 (2H, br. s), 2.06 (3H, s). Mass Spectrum (ESI) m/e=587.2 (M+1).

Provenance & Evidence