HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-(Dimethylamino)ethanol → 2-Bromo-6-chloro-4-methylpyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-(Dimethylamino)ethanol | HCID 7902 | — |
| Reactant | Carbon tetrabromide | HCID 11205 | — |
| Reactant | 2-Chloro-4-methylpyridine | HCID 77248 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 2-Bromo-6-chloro-4-methylpyridine | HCID 11117234 | — |
Reaction Steps
Starting with 2-chloro-4-methylpyridine II, treatment with n-butyllithium in the presence of N,N-dimethylaminoethanol in hexane, followed by addition of carbon tetrabromide in THF affords 2-bromo-6-chloro-4-methylpyridine III. Compound III undergoes a palladium coupling with boronic acid IV in the presence of a base, such as Na2CO3, in a suitable solvent, such as DME, to give chloropyridine V.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07968725B2 |
| Source dataset | uspto-grants-2011_06 |
| ORD ID | ord-e75ca494381245ac8e0a1cb0c2f4ee1c |
| Source note | uspto-grants-2011_06 |