2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 50908277, 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, 0.044 mmol), 2,5-dimorpholinopyridin-3-amine (0.088 g, 0.33 mmol), 4-chloro-2-(6-(cyclopropylmethoxy)pyridin-3-yl)-5,7-difluoro-3-methylquinoline (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 1.6 h. The crude product was purified by column chromatography on silica gel (0 to 100% DCM/MeOH/ammonium hydroxide (90/9/1)) to give the desired product 2-(6-(cyclopropylmethoxy)-pyridin-3-yl)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methylquinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (1H, d, J=1.8 Hz), 8.00 (1H, dd, J=8.5, 2.4 Hz), 7.77 (1H, d, J=4.9 Hz), 7.63 (1H, dd, J=10.0, 1.6 Hz), 7.55 (1H, d, J=2.7 Hz), 7.41-7.49 (1H, m), 6.98 (1H, d, J=8.6 Hz), 6.43 (1H, d, J=2.7 Hz), 5.75 (1H, s), 4.18 (2H, d, J=7.2 Hz), 3.57-3.84 (8H, m), 3.15 (2H, br. s.), 2.99 (4H, m), 2.83 (2H, br. s.), 2.09 (3H, s), 1.23-1.34 (1H, m), 0.54-0.62 (2H, m), 0.33-0.41 (2H, m). Mass Spectrum (ESI) m/e=589.3 (M+1).

Provenance & Evidence