HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Ethyl 3-(3-(((2-((1-cyanocyclopentyl)methyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)-3-cyclopropylpropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Ethyl 3-cyclopropyl-3-(3-(((methylsulfonyl)oxy)methyl)phenyl)propanoate | HCID 117759650 | — |
| Reactant | 1-((2'-Fluoro-4-hydroxy-5'-methoxybiphenyl-2-yl)methyl)cyclopentanecarbonitrile | HCID 117760159 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Ethyl 3-(3-(((2-((1-cyanocyclopentyl)methyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)-3-cyclopropylpropanoate | HCID 117760129 | 66.8% |
Reaction Steps
To a solution of 1-((2′-fluoro-4-hydroxy-5′-methoxybiphenyl-2-yl)methyl)cyclopentanecarbonitrile (128 mg) and ethyl 3-cyclopropyl-3-(3-(((methylsulfonyl)oxy)methyl)phenyl)propanoate (197 mg) in DMF (5.0 mL) was added cesium carbonate (261 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (146 mg) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382188B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-73f843fed8c74e9eac91862041a83be5 |
| Source note | uspto-grants-2016_07 |