Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | (Trifluoromethyl)trimethylsilane | HCID 552549 | — |
| Reactant | HCID 58542506 | HCID 58542506 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58542524 | HCID 58542524 | 86.9% |
Reaction Steps
268 mg (1.40 mmol) of copper(I) iodide and 65.3 mg (1.12 mmol) of potassium fluoride are initially introduced into a heat-dried vial under argon, and 3 ml of N,N-dimethylformamide and 300 mg (0.93 mmol) of ethyl-3-cyclopropyl-4-iodo-1-methyl-1H-pyrazole-5-carboxylate and 0.28 ml (1.87 mmol) of trimethyl(trifluoromethyl)silane are added. The reaction mixture is degassed in the ultrasound, flushed with argon and the closed via is heated at 80° C. for three hours. The cooled reaction solution is admixed with a small amount of water, diluted with ethyl acetate, filtered over silica gel (ethyl acetate) and concentrated by evaporation on a rotary evaporator. Chromatographic purification on silica gel gives 212 mg of ethyl 3-cyclopropyl-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate (86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946234B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-fbd005f322f94ea4a5f2cd94ca0ce11c |
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| Source note | uspto-grants-2015_02 |
|---|