HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Potassium Carbonate → HCID 86698752, Verbindung
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 3-(4-Bromophenyl)propan-1-ol | HCID 10560614 | — |
| Edukt | 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole | HCID 86698733 | — |
| Katalysator | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | HCID 86698752 | HCID 86698752 | 33,6% |
Reaktionsschritte
To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (100 mg, 0.379 mmol) in dioxane (2 mL) and DMF (0.1 mL) was added N,N-dimethylformiminium chloride (180 mg, 0.36 mmol). The resulting mixture was stirred at room temperature for 20 min. The reaction was quenched with 2.0N potassium carbonate (1.5 mL, 3.0 mmol), then 3-(4-bromophenyl)propan-1-ol (81.5 mg, 0.379 mmol) and Pd(dppf)Cl2 (28 mg, 0.037 mmol) were added, then heated to 90° C. for 30 min. The reaction mixture was extracted with EtOAc (3 mL×3), combined the organic layers and concentrated in vacuo to afford the title compound (40 mg, 27% yield) after purification via preparative TLC.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08889730B2 |
| Quelldatensatz | uspto-grants-2014_11 |
| ORD ID | ord-023be1fe6e624196b641c492c0d3796f |
| Quellennotiz | uspto-grants-2014_11 |