Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromoethyldiethylammonium bromide | HCID 70607 | — |
| Reactant | Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate | HCID 66771917 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86700070 | HCID 86700070 | 23.9% |
Reaction Steps
Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (270 mg) was suspended in DMF (3.0 ml). Cesium carbonate (1180 mg) and 2-bromo-N,N-diethylethylamine hydrobromide (405 mg) were added sequentially, and the mixture was stirred at 50° C. for six hours. A 1 N aqueous hydrochloric acid solution was added under ice cooling, and the insoluble matter was then removed by filtration through celite. After 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 89 mg of the title compound as an oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08933103B2 |
|---|
| Source dataset | uspto-grants-2015_01 |
|---|
| ORD ID | ord-54f910477f6940d78bfaa3b34f6dec4f |
|---|
| Source note | uspto-grants-2015_01 |
|---|