Buchwald–Hartwig amination: Ethyl 7-bromobenzofuran-2-carboxylate → Ethyl 7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate
40% yield, run at 95 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Ethyl 7-bromobenzofuran-2-carboxylate | C₁₁H₉BrO₃ | |
| Reactant | Piperazine, 2-pyridylethyl- | C₁₁H₁₇N₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate | C₂₂H₂₅N₃O₃ | 39.97% |
Conditions
- Temperature
- 95 °C
Yield
- 40% of Ethyl 7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
12/01 2009 15:21:58 +0100 To ethyl 7-bromobenzofuran-2-carboxylate (0.900 g, 3.34 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (0.672 g, 3.51 mmol) in dry degassed dioxane (13 mL) were added Cesium carbonate (1.417 g, 4.35 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.159 g, 0.33 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.153 g, 0.17 mmol) under argon and the reaction heated at 95°C o/n. All starting material consumed. Water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (MgSO4), filtered and evaporated. The crude was purified by flash chrom. (SiO2; DCM/MeOH 95/5) to give EN02198-25-001: 47.3 mg (fraction 12 from the flash) of the product as a pale yellow solid. Th
The source
This record comes from experimental reaction archive (ord-61dd76cabf5f48cb8028fe718c7f9d72). Open the source and check it against what is on this page.
experimental reaction archive record ord-61dd76cabf5f48cb8028fe718c7f9d72 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
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