Electric Literature of 39806-90-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 39806-90-1 as follows.
1-Methyl-4-((trimethylsilyl)ethynyl)-1H-pyrazole (19) 1-Methyl-4-iodo-pyrazole (18) (5.0 g 24.04 mmole) was dissolved in DMF (32 mL) and ethynyltrimethylsilane (4.76 mL, 3.31 g, 33.7 mmole) was added followed by diisopropylamine (4.46 mL, 3.21 g 31.78 mmole), copper(I) iodide (304 mg 1.59 mmole) and triphenylphosphine (1.26 g 4.81 mmole). The reaction was flushed with argon. Palladium acetate (351 mg 1.56 mmole) was added and the reaction was again flushed with argon. It was heated at 60 C. for 60 mins. The reaction was cooled, added to water (350 ml) and extracted with ether (3*100 mL). The organic solution was filtered from a brown solid which was washed with a little more ether. The organic solution was washed with water (3*80 mL), brine, dried and evaporated. The crude product was flash chromatographed (silica) using 1:4 ethyl acetate:cyclohexane and then 1:3 ethyl acetate:cyclohexane to give the title compound as a solid (2.85 g 67%). 1H-NMR (CDCl3, 500 MHz): delta 0.24 (s, 9H), 3.87 (s, 3H), 7.50 (s, 1H), 7.58 (s, 1H).
According to the analysis of related databases, 39806-90-1, the application of this compound in the production field has become more and more popular.