HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Potassium Carbonate → 6-[(5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-3-methyl-2-pyridinecarbonitrile
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 6-(Chloromethyl)-3-methyl-2-pyridinecarbonitrile | HCID 55298148 | — |
| Edukt | (5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)boronic acid | HCID 59384250 | — |
| Katalysator | HCID 178418397 | HCID 178418397 | — |
| Lösungsmittel | Ethanol | HCID 702 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Produkt | 6-[(5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-3-methyl-2-pyridinecarbonitrile | HCID 68456587 | 64% |
Reaktionsschritte
To a solution of 6-(Chloromethyl)-3-methyl-2-pyridinecarbonitrile (132.5 mg) in dry toluene (4 ml) and ethanol (4 ml) was added (5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)boronic acid (250 mg), potassium carbonate (330 mg) and tetrakis(triphenylphosphine)palladium(0) (92 mg) and the mixture stirred under reflux for 2.5 hours. Solvent was removed in vacuo and water (20 ml) and ether (20 ml) added. Insoluble solid was filtered over Celite and washed with ether. The aqueous layer was further extracted with ether (15 ml) and the combined extracts washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by mass-directed autopreparation to afford the title compound (204 mg, 64%) as a white solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07759369B2 |
| Quelldatensatz | uspto-grants-2010_07 |
| ORD ID | ord-5f54190645cd482d812a81eec6280f73 |
| Quellennotiz | uspto-grants-2010_07 |