Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | 5-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole | HCID 15462077 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 21188055 | HCID 21188055 | — |
Reaction Steps
To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (200 mg, the compound of Example A1) in triethylamine (2 ml) and dimethylformamide (1 ml) at room temperature was added propargyl alcohol (0.2 ml), cuprous iodide (10 mg) and bis(triphenylphosphine)palladium(II) chloride (20 mg). The reaction mixture was heated at 70° C. for two hours. The reaction mixture was partitioned between ether (10 ml) and water (10 ml). The organic layer was separated, washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel eluted with ether:dichloromethane (10:1) to provide the title compound as a pale yellow solid m.p. 237-9° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06255333B1 |
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| Source dataset | uspto-grants-2001_07 |
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| ORD ID | ord-0ab16ba369ef48218729708628323cfd |
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| Source note | uspto-grants-2001_07 |
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