Trimethylsilylacetylene → Benzyl 2-amino-3-ethynylbenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of benzyl 2-amino-3-iodobenzoate (5.56 g), trimethylsilylacetylene (3.26 mL), bis(triphenylphosphine)palladium(II) dichloride (0.350 g) and copper iodide (0.299 g) in triethylamine (75 mL) was stirred under a nitrogen atmosphere at room temperature for 1.5 hr. The reaction mixture was diluted with diisopropyl ether, washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (75 mL), 1.0 M tetrabutylammonium fluoride (25 mL) was added under ice-cooling, and the mixture was stirred at 0° C. for 1.5 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-15:85) to give the title compound (3.06 g, yield 77%) as colorless crystals. melting point 42-43° C.

Provenance & Evidence