Trimethylsilylacetylene → 6-[(trimethylsilyl)ethynyl]-1-benzoyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

The synthesis was performed with reference to the known literature (Bulletin of the Chemical Society of Japan, Vol. 65, p. 2992, 1992). A solution of 1-benzoyl-6-bromo-1H-pyrrolo[2,3-b]pyridine (0.30 g, 1.0 mmol) in triethylamine (25 mL) was added with dichlorobis(triphenylphosphine)palladium(II) (0.036 g, 0.050 mmol), and copper(I) iodide (0.016 g, 0.085 mmol) under an argon atmosphere. Then, the mixture was slowly added with trimethylsilylacetylene (0.20 g, 2.0 mmol), and then the mixture was stirred at room temperature for 24 hours. Triethylamine was evaporated under reduced pressure, the residue was dissolved in ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (100:0→90:10)) to obtain 6-[(trimethylsilyl)ethynyl]-1-benzoyl-1H-pyrrolo[2,3-b]pyridine (0.045 g, 14%).

Provenance & Evidence