反应详情

温度

60 °C

2-(4-Iodo-1H-pyrazol-1-yl)-N,N-dimethylacetamide (Preparation 99, 0.68 g, 2.42 mmol) and trimethylsilylacetylene (0.326 g, 3.32 mmol) were dissolved in dry DMF (5 ml) and placed under argon. Diisopropylamine (0.47 ml, 3.3 mmol), copper (1) iodide (30 mg, 0.16 mmol), triphenylphosphine (126 mg, 0.242 mmol) and palladium acetate (40 mg, 0.16 mmol) were added and the flask was flushed with argon. The reaction was heated to 60° C. for 1 hour. The reaction was cooled to room temperature and diluted with ethyl acetate (30 ml). The organic solution was washed with water, brine, dried over sodium sulphate and filtered. The solvent was removed in vacuum and the crude purified on silica gel column chromatography eluting with neat ethyl acetate to afford the title compound as a pale yellow powder (0.55 g, 91%). 1H-NMR (500 MHz, CDCl3): δ 0.21 (s, 9H), 2.96 (s, 3H), 3.04 (s, 3H), 4.92 (s, 2H), 7.59 (s, 1H), 7.65 (s, 1H).

1. customthe flask was flushed with argon
2. temperatureThe reaction was cooled to room temperature
3. additiondiluted with ethyl acetate (30 ml)
4. washThe organic solution was washed with water, brine
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. customThe solvent was removed in vacuum
8. customthe crude purified on silica gel column chromatography
9. washeluting with neat ethyl acetate