Buchwald–Hartwig amination: Ethyl 7-bromobenzofuran-2-carboxylate → Ethyl 7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate
70% 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 | 69.5% |
Conditions
- Temperature
- 95 °C
Yield
- 70% of Ethyl 7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate.
Procedure
Copied from the source record, unedited
17/02 2009 12:47:13 +0100 To ethyl 7-bromobenzofuran-2-carboxylate (1.50 g, 5.57 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (1.120 g, 5.85 mmol) in dry degassed dioxane (20 mL) were added Cesium carbonate (2.361 g, 7.25 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.266 g, 0.56 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.255 g, 0.28 mmol) under argon and the reaction heated at 95°C o/n. The reaction was allowed to reach rt. Starting material left 18/02 2009 14:51:20 +0100 Additional2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.266 g, 0.56 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.255 g, 0.28 mmol) were added and the reaction stirred at 95°C o/n. The reaction mixture was pooled with the reaction mixture in EN02198-44. Water and DCM wer
The source
This record comes from experimental reaction archive (ord-3e4ae9ef9d2f47b2b03f41aafafa9bc4). Open the source and check it against what is on this page.
experimental reaction archive record ord-3e4ae9ef9d2f47b2b03f41aafafa9bc4 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
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.