2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631554, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.022 g, 0.045 mmol), 2,5-dimorpholinopyridin-3-amine (0.090 g, 0.34 mmol), 4-chloro-2-(2,4-dimethylphenyl)-5,7-difluoro-3-methylquinoline (0.090 g, 0.28 mmol), Pd2dba3 (10.4 mg, 0.011 mmol) and sodium tert-butoxide (0.068 g, 0.71 mmol) in toluene (2.8 mL) at 120° C. for 3.3 h. The crude product was purified by column chromatography on basic alumina (0 to 50% hexanes/EtOAc) to give the desired product 2-(2,4-dimethylphenyl)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methylquinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.46 (1H, s), 8.70 (1H, d, J=4.8 Hz), 8.02 (1H, td, J=7.8, 1.8 Hz), 7.98 (1H, d, J=5.7 Hz), 7.89 (1H, dt, J=7.8, 1.2 Hz), 7.67 (1H, br. dd, J=2.2, 1.8 Hz), 7.65 (2H, dt, J=8.4, 1.6 Hz), 7.52 (1H, ddd, J=7.6, 4.9, 1.4 Hz), 7.47 (1H, ddd, J=12.1, 9.2, 2.5 Hz), 6.10 (1H, br. s), 3.48 (4H, br s), 3.40-3.30 (8H, m), 2.27 (3H, s). Mass Spectrum (ESI) m/e=546.3 (M+1).

Provenance & Evidence