N-methyl-2-pyrrolidone → 3-((Trimethylsilyl)ethynyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a NMP (120 mL) solution of 2-amino-3-bromopyridine (5.72 g, 33.1 mmol) were added trimethylsilylacetylene (9.36 mL, 66.2 mmol), tetrakis(triphenylphosphine)palladium(0) (1.91 g, 1.66 mmol), copper(I) iodide (630 mg, 3.31 mmol), and N,N-diisopropylethylamine (11.5 mL, 66.2 mmol) at room temperature, which was stirred for 6 hours at 70° C. under a nitrogen atmosphere. Water was added at 0° C. to the reaction solution, and then extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine, after which it was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1) to obtain the titled compound (5.9 g).

Provenance & Evidence