HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,6-Dibromopyridine → 2-Bromo-6-[2-(3-methoxycarbonylphenyl)ethinyl]-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,6-Dibromopyridine | HCID 12274 | — |
| Reactant | 3-Ethynylbenzoic acid methyl ester | HCID 11275159 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 2-Bromo-6-[2-(3-methoxycarbonylphenyl)ethinyl]-pyridine | HCID 19966486 | 23.8% |
Reaction Steps
A solution of 15.1 g of 2,6-dibromopyridine in 500 ml of triethylamine is mixed under ice cooling with 10.2 g of 3-ethinylbenzoic acid methyl ester, 1.1 g of bis-(triphenylphosphine)-palladium(II) chloride and 150 mg of copper(I) iodide and the mixture is stirred for 1 hour. Then, the ice bath is removed and it is stirred for 48 hours at room temperature. The precipitate is filtered off, the filtrate is evaporated to dryness, mixed with water and shaken out with ethyl acetate. The organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-12% ethyl acetate. 4.8 g of 2-bromo-6-[2-(3-methoxycarbonyiphenyl)-ethinyl]-pyridine of melting point 12°-126° C. is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05614634 |
| Source dataset | uspto-grants-1997_03 |
| ORD ID | ord-4bb28497933843ff97b13aab94eb29fe |
| Source note | uspto-grants-1997_03 |