Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Chloro-2-methylpropan-2-ol | HCID 68409 | — |
| Reactant | Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate | HCID 66771917 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86700069 | HCID 86700069 | — |
Reaction Steps
Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (400 mg) was suspended in DMF (5.0 ml). Cesium carbonate (1200 mg), 1-chloro-2-methyl-2-propanol (345 μl) and tetra-n-butylammonium iodide (56 mg) were added sequentially, and the mixture was stirred at 70° C. for 10 hours. A 1 N aqueous hydrochloric acid solution was added at room temperature. The insoluble matter was removed by filtration through celite, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->60:1 (v/v)] to give 57 mg of the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933103B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-9f2be6c5a403401aabad39c52e907e57 |
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| Source note | uspto-grants-2015_01 |
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