HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 3-Bromo-5-ethylpyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3,5-Dibromopyridine | HCID 69369 | — |
| Reactant | Ethylboronic acid | HCID 521157 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Catalyst | HCID 178418778 | HCID 178418778 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Bromo-5-ethylpyridine | HCID 642804 | — |
Reaction Steps
3,5-dibromo-pyridine (0.4 g, 1.688 mmol), potassium carbonate (0.7 g, 5.064 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.138 g, 0.169 mmol), silver(I) oxide (0.902 g, 4.22 mmol), ethyl boronic acid (0.150 g, 2.03 mmol) and THF (8 ml) are mixed together, purged with argon and heated to reflux overnight. After cooling to room temperature the reaction mixture is filtered through Celite® (filter agent) washing with DCM. The DCM is reduced in vacuo and the residue is purified by flash chromatography by loading onto a 20 g silica column eluting with DCM to afford the title compound, [MH+ 185.91 and 187.91].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08053574B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-02fb406c602a4af6b6e2a0b34182214a |
| Source note | uspto-grants-2011_11 |