HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cesium carbonate → tert-Butyl 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)phenylcarbamate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2774010 | — |
| Edukt | tert-Butyl 3-(bromomethyl)phenylcarbamate | HCID 14523558 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | tert-Butyl 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)phenylcarbamate | HCID 70983056 | 59% |
Reaktionsschritte
To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.88 g, 4.54 mmol) in acetonitrile (20 mL) was added cesium carbonate (4.43 g, 13.61 mmol) and tert-butyl 3-(bromomethyl)phenylcarbamate (1.298 g, 4.54 mmol). The reaction was stirred at room temperature for 3 h. After this time, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The aqueous phase was extracted with CHCl3. The combined organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The resulting residue was purified by (0-100% ethyl acetate:hexanes) to afford the title compound (1.06 g, 2.65 mmol, 59% yield) as a colorless oil. LCMS, [M+H]+=400.3.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09062028B2 |
| Quelldatensatz | uspto-grants-2015_06 |
| ORD ID | ord-f0ebad78e4424741ba89cd3b973db86b |
| Quellennotiz | uspto-grants-2015_06 |