2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 67508691, 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 (0.023 g, 0.048 mmol), 5-morpholinopyridin-3-amine (0.064 g, 0.36 mmol), 4-chloro-2-(6-ethoxypyridin-3-yl)-5,7-difluoro-3-methylquinoline (0.1 g, 0.30 mmol), Pd2dba3 (0.011 g, 0.012 mmol) and sodium tert-butoxide (0.072 g, 0.75 mmol) in toluene (3.0 mL) at 100° C. for 43 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-ethoxypyridin-3-yl)-5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (1H, d, J=1.4 Hz), 8.45-8.47 (1H, dd, J=2.4, 0.6 Hz), 8.02 (1H, dd, J=8.5, 2.4 Hz), 7.80 (1H, d, J=2.5 Hz), 7.62 (1H, m), 7.59 (1H, d, J=2.2 Hz), 7.39-7.46 (1H, m), 6.92-6.96 (1H, d, J=8.4, 0.6 Hz), 6.57 (1H, t, J=2.4 Hz), 4.39 (2H, q, J=7.0 Hz), 3.67-3.76 (4H, m), 3.05-3.13 (4H, m), 2.16 (3H, s), 1.36 (3H, t, J=7.0 Hz). Mass Spectrum (ESI) m/e=478.3 (M+1).

Provenance & Evidence