2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631509, compound

Participants

Reaction Steps

The Buchwald coupled product was prepared according to Procedure S using of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.020 g, 0.043 mmol), 5-morpholinopyridin-3-amine (0.057 g, 0.32 mmol), 4-(5-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2-yl)morpholine (0.1 g, 0.27 mmol), Pd2dba3 (0.010 g, 0.011 mmol) and sodium tert-butoxide (0.064 g, 0.67 mmol) in toluene (2.7 mL) at 100° C. for 2.5 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 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(6-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (1H, dd, J=2.5, 0.6 Hz), 8.45 (1H, d, J=1.6 Hz), 7.92 (1H, dd, J=8.9, 2.4 Hz), 7.79 (1H, d, J=2.5 Hz), 7.57-7.62 (2H, m), 7.35-7.42 (1H, m), 6.96 (1H, d, J=8.6 Hz), 6.56 (1H, t, J=2.3 Hz), 3.71 (8H, dt, J=12.1, 4.8 Hz), 3.53-3.59 (4H, m), 3.05-3.11 (4H, m), 2.18 (3H, s). Mass Spectrum (ESI) m/e=519.2 (M+1).

Provenance & Evidence