Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Ethynylpyridine | HCID 642801 | — |
| Reactant | HCID 178517752 | HCID 178517752 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86680837 | HCID 86680837 | 12.4% |
Reaction Steps
A mixture of 0.29 g of 3-iodo-5-(trifluoromethyl)pyridin-2-ol, 0.35 g of 4-ethynylpyridine, 20 mg of dichlorobis(triphenylphosphine)palladium(II), 0.30 g of triethylamine, 15 mg of copper(I) iodide and 5 ml of DMF was stirred under a nitrogen atmosphere at room temperature for 2 hours. To the reaction mixture were added water, then t-butyl methyl ether, and the mixture was filtered through Celite (registered trademark). The filtrate was separated, and the organic layer was dried over sodium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel preparative thin-layer chromatography to obtain 33 mg of 2-(pyridin-4-yl)-5-trifluoromethyl-furo[2,3-b]pyridine (hereinafter, referred to as “Present Active Compound 13”).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796306B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-8c5f652b28714d81b57bf7126d931c0d |
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| Source note | uspto-grants-2014_08 |
|---|