Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(Bromomethyl)pyridine hbr | HCID 12752219 | — |
| Reactant | Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate | HCID 66771917 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86700039 | HCID 86700039 | 46.7% |
Reaction Steps
4-(Bromomethyl)pyridine hydrobromide (290 mg) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (200 mg) and cesium carbonate (998 mg) in DMF (5 ml) at room temperature. The reaction mixture was stirred at 100° C. overnight. The reaction mixture was returned to room temperature and diluted by adding ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, the residue was purified by silica gel column chromatography [chloroform:methanol=10:0->19:1->9:1 (v/v)], and the eluate was concentrated under reduced pressure. The residue was purified by PLC [dichloromethane:methanol=10:1 (v/v)] to give 126 mg of the title compound as an oily substance.
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-374a365b1d1840ce8a878c3e215d4194 |
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| Source note | uspto-grants-2015_01 |
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