HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Ethyl 3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)-4-methylphenyl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ethyl 3-(3-hydroxy-4-methylphenyl)propanoate | HCID 117759964 | — |
| Reactant | 6-(Chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine | HCID 117759999 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Ethyl 3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)-4-methylphenyl)propanoate | HCID 117760300 | 88.4% |
Reaction Steps
To a solution of 6-(chloromethyl)-2-(2,2-dimethylpropyl)-3-(2-fluoro-5-methoxyphenyl)pyridine (350 mg) in acetonitrile (30 ml) were added ethyl 3-(3-hydroxy-4-methylphenyl)propanoate (191 mg) and cesium carbonate (597 mg), and the mixture was heated under reflux for 15 hr. The reaction mixture was concentrated, and water was added to the residue. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (400 mg) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181186B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-180c9ecd96164a4f9f934ed9cd1af282 |
| Source note | uspto-grants-2015_11 |