Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Trimethylsilyl cyanide | HCID 82115 | — |
| Edukt | 3-(benzyloxy)-5-bromopyridine N-oxide | HCID 58213489 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Produkt | 5-(Benzyloxy)-3-bromopicolinonitrile | HCID 67117707 | — |
Reaktionsschritte
To a solution of 53-(benzyloxy)-5-bromopyridine 1-oxide (from step 2) (1.0 eq.) in acetonitrile (0.2 M) was added trimethylsilyl cyanide (TMSCN) (4.0 eq.) and triethylamine (3.0 eq.). The reaction was heated at 100° C. overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH® system (ISCO) using 0-40% ethyl acetate in hexane to give a mixture of two benzoxy regioisomers, one of which was the desired product. The mixture was carried onto the next step without further purification.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US08895577B2 |
|---|
| Quelldatensatz | uspto-grants-2014_11 |
|---|
| ORD ID | ord-79c3e6c71bb74976b38875d78721c99b |
|---|
| Quellennotiz | uspto-grants-2014_11 |
|---|