Trimethylsilylacetylene → 3-Nitro-5-((trimethylsilyl)ethynyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-bromo-5-nitropyridine (1.0 g, 4.90 mmol), Pd(Ph3P)4 (0.57 g, 0.49 mmol), and copper iodide (0.19 g, 0.98 mmol) in triethylamine (30 mL) was added ethynyltrimethylsilane (1.0 mL, 7.35 mmol) and the reaction was purged with N2. The mixture was stirred at 80° C. for 2 h. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with saturated solutions of NaHCO3 and NaCl. The organic layer was concentrated to afford the crude product (1.72 g) as a light brown solid: ESI MS m/z 221 [C10H12N2O2Si+H]+.

Provenance & Evidence