2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631398, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.015 g, 0.031 mmol), 2,5-dimorpholinopyridin-3-amine (0.062 g, 0.23 mmol), 4-chloro-2-(6-(4,4-difluoropiperidin-1-yl)pyridin-3-yl)-5,7-difluoro-3-methylquinoline (0.08 g, 0.20 mmol) and Pd2dba3 (0.007 g, 0.008 mmol) and sodium tert-butoxide (0.047 g, 0.49 mmol) in toluene (2.0 mL) at 100° C. for 73 h. The crude product was purified by column chromatography on silica gel (0 to 100% DCM/methanol/ammonium hydroxide (90/9/1)) to give the desired product 2-(6-(4,4-difluoropiperidin-1-yl)pyridin-3-yl)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methylquinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (1H, d, J=2.2 Hz), 7.90 (1H, dd, J=8.9, 2.4 Hz), 7.76 (1H, d, J=5.9 Hz), 7.57-7.63 (1H, m), 7.55 (1H, d, J=2.7 Hz), 7.38-7.46 (1H, m), 7.10 (1H, d, J=8.8 Hz), 6.41 (1H, d, J=2.3 Hz), 3.80 (4H, m), 3.60-3.77 (8H, m), 3.13 (2H, br. s.), 2.94-3.04 (4H, m), 2.82 (2H, br. s.), 2.13 (3H, s), 2.03 (4H, m). Mass Spectrum (ESI) m/e=638.2 (M+1).

Provenance & Evidence