HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cesium carbonate → (S)-methyl 6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | (2S)-1,1,1-Trifluoropropan-2-ol | HCID 6999971 | — |
| Edukt | Methyl 5-bromo-6-(4-chlorophenyl)pyrazine-2-carboxylate | HCID 86619571 | — |
| Lösungsmittel | Dimethyl Sulfoxide | HCID 679 | — |
| Produkt | (S)-methyl 6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylate | HCID 66678867 | 77,6% |
Reaktionsschritte
To a solution of methyl 5-bromo-6-(4-chlorophenyl)pyrazine-2-carboxylate (0.847 g, 2.59 mmol, Eq: 1.00) in dry DMSO (8 ml) was added cesium carbonate (1.54 g, 2.84 mmol, Eq: 1.1) and (S)-1,1,1-trifluoro-2-propanol (324 mg, 233 μl, 2.84 mmol, Eq: 1.1) and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the organic phase was dried over MgSO4 evaporated and purified by flash chromatography (silica gel, 100 g, 10% to 50% ethyl acetate in heptane) to yield the title compound as light yellow oil (0.724 g, 77.6%). MS (EI): 361.1 (M+H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08669254B2 |
| Quelldatensatz | uspto-grants-2014_03 |
| ORD ID | ord-981bb6d9a53d429b8ef03f5a4dccb3e7 |
| Quellennotiz | uspto-grants-2014_03 |