2,6-Di-tert-butyl-4-methylphenol → HCID 86699738, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of trifluoro-methanesulfonic acid [2-[(4-chlorophenyl)-methyl-carbamoyl]-3-methyl-5-morpholin-4-yl-phenyl]ester (synthesized according to the method described in section a) of example 12) (1.0 g, 2.03 mmol) in dioxane (50 ml) are added 2,6-di-tert-butyl-4-methylphenol (0.044 g, 0.20 mmol), lithium chloride (0.688 g, 16.3 mmol) and tributyl-1-cyclopenten-1-yl-stannane (1.46 g, 4.06 mmol). The mixture is degassed and flushed with argon for 30 min followed by the addition bis(triphenylphosphine)palladiumchloride (0.17 g, 0.24 mmol). The resulting mixture is heated at 120° C. for 16 h. The reaction mixture is diluted with water (30 ml) and extracted with ethyl acetate (3×50 ml). The organic layer is washed with water (20 ml), saturated potassium fluoride solution (2×20 ml), brine (20 ml) and dried over anhydrous sodium sulfate. Evaporation under vacuum afforded the crude product, which is purified by column chromatography (silica gel-10% KF, 20% ethyl acetate/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-cyclopenten-1-yl-6-methyl-4-morpholin-4-yl-benzamide (0.50 g, 1.22 mmol, 60%).

Provenance & Evidence