2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631140, 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, 0.049 mmol), 2,5-dimorpholinopyridin-3-amine (0.098 g, 0.37 mmol), 4,8-dichloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.1 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 120° C. for 3 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product 8-chloro-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.68 (1H, d, J=4.6 Hz), 8.18 (1H, d, J=8.0 Hz), 7.93 (1H, td, J=7.7, 1.8 Hz), 7.79 (1H, br. d., J=10.4 Hz), 7.64 (1H, d, J=2.5 Hz), 7.40 (1H, dd, J=7.4, 4.6 Hz), 7.11 (1H, dd, J=13.0, 8.7 Hz), 6.45 (1H, br. s.), 3.93 (4H, s), 3.81 (4H, app. dd, J=4.1, 2.5 Hz), 3.25 (4H, br. s), 3.09 (4H, app. dd, J=5.9, 3.9 Hz), 2.32 (3H, s). Mass Spectrum (ESI) m/e=553.2 (M+1).

Provenance & Evidence