HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-Bromo-6-methylpyridine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilyl cyanide | HCID 82115 | — |
| Reactant | 5-Bromo-2-methylpyridin-1-ium-1-olate | HCID 817164 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 3-Bromo-6-methylpyridine-2-carbonitrile | HCID 21952747 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
To a solution of 5-bromo-2-methylpyridine 1-oxide (from step 1) (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 0-50% ethyl acetate in hexane to give 3-bromo-6-methylpicolinonitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08466167B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-a943cd0373b140c5ba2431080f32a2c2 |
| Source note | uspto-grants-2013_06 |