2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 67508710, 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 (0.024 g, 0.050 mmol), 5-morpholinopyridin-3-amine (0.067 g, 0.37 mmol), 4-chloro-5,7-difluoro-2-(5-methoxypyridin-3-yl)-3-methylquinoline (0.1 g, 0.31 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.075 g, 0.78 mmol) in toluene (3.1 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 5,7-difluoro-2-(5-methoxypyridin-3-yl)-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.51 (1H, d, J=1.8 Hz), 8.39-8.45 (2H, m), 7.80 (1H, d, J=2.3 Hz), 7.59-7.69 (3H, m), 7.43-7.51 (1H, m), 6.60 (1H, t, J=2.3 Hz), 3.90 (3H, s), 3.67-3.77 (4H, m), 3.05-3.17 (4H, m), 2.11 (3H, s). Mass Spectrum (ESI) m/e=464.1 (M+1).

Provenance & Evidence