N-methyl-2-pyrrolidone → 2-Nitro-5-((trimethylsilyl)ethynyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a NMP solution (20 mL) of 5-bromo-2-nitropyridine (1.00 g, 4.93 mmol) were added trimethylsilyl acetylene (1.4 mL), tetrakis(triphenylphosphine)palladium(0) (110 mg), copper(I) iodide (38 mg), and N,N-diisopropylethylamine (1.7 mL) at room temperature, which was stirred under a nitrogen atmosphere for 4 hours at 65° C. Water was added at 0° C. to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered, after which the solvent was evaporated from the filtrate under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=6:1) to obtain the titled compound (490 mg).

Provenance & Evidence