Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Iodo-1-methyl-1H-pyrazole-5-carbaldehyde | HCID 17853460 | — |
| Reactant | HCID 86684886 | HCID 86684886 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86684885 | HCID 86684885 | — |
Reaction Steps
A mixture of 4-iodo-1-methyl-1H-pyrazol-5-carbaldehyde (500 mg), 4-ethynylbenzenesulfonic acid (383 mg), copper(I) iodide (20 mg), bis(triphenylphosphine)palladium(II) dichloride (149 mg), triethylamine (600 μL) and dimethylformamide (10 mL) was stirred at 80° C. for 4 hours. Thereafter, the reaction solution was filtrated with Celite, and the filtrate was then washed with water. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=99:1 to 90:10), so as to obtain the title compound (580 mg) in the form of a light yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08642626B2 |
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| Source dataset | uspto-grants-2014_02 |
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| ORD ID | ord-895ceaa5b5be4090ad28cadeb13629e0 |
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| Source note | uspto-grants-2014_02 |
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