2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631523, compound

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Reaction Steps

The Buchwald coupled product was prepared according to Procedure H using dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.025 g, 0.052 mmol), 2,5-dimorpholinopyridin-3-amine (0.103 g, 0.39 mmol), 4-chloro-5,7-difluoro-2-(2-fluorophenyl)-3-methylquinoline (0.1 g, 0.33 mmol), Pd2dba3 (0.012 g, 0.013 mmol) and sodium tert-butoxide (0.078 g, 0.81 mmol) in toluene (3.3 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 N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-2-(2-fluorophenyl)-3-methylquinolin-4-amine. 1H NMR (400 MHz, CDCl3-d) δ ppm 7.59-7.68 (3H, m), 7.47-7.54 (1H, m), 7.36 (1H, td, J=7.5, 1.2 Hz), 7.20 (1H, m,), 7.05 (1H, ddd, J=13.6, 8.6, 2.6 Hz), 6.42 (1H, br. s.), 3.93 (4H, br. s.), 3.83 (4H, m), 3.40 (2H, br. s.), 3.08 (4H, br. s.), 3.01 (2H, br s), 2.07 (3H, d, J=2.0 Hz). Mass Spectrum (ESI) m/e=536.2 (M+1).

Provenance & Evidence