Buchwald–Hartwig amination: Ethyl 4-bromobenzofuran-2-carboxylate → Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate
0% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Ethyl 4-bromobenzofuran-2-carboxylate | C₁₁H₉BrO₃ | |
| Reactant | 1-Benzylpiperazine | C₁₁H₁₆N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Di-tert-butylphosphino)biphenyl | C₂₀H₂₇P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate | C₂₂H₂₄N₂O₃ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl; Bis(dibenzylideneacetone)palladium | Cesium carbonate | 1,4-Dioxane | 95 °C | — | 27% |
| 2-(Di-tert-butylphosphino)biphenyl; Bis(dibenzylideneacetone)palladium | Cesium carbonate | Toluene | 100 °C | — | 0% (this run) |
| Binap, (A+-)-; Bis(dibenzylideneacetone)palladium | potassium 2-methylpropan-2-olate | Toluene | 50 °C | — | 0% |
Procedure
Copied from the source record, unedited
**Purpose:** Buchwald-Hartwig coupling using unpurified ethyl 4-bromobenzofuran-2-carboxylate. The analysis on crude 4-bromobenzofuran-2-carboxylate shows traces of non cyclized and non aromoatized by-products. 2010-03-10 16:38:11: To a 25 mL rounbottomed flask was added ethyl 4-bromobenzofuran-2-carboxylate (1 g; 3.72 mmol) and toluene (10 mL/g-bulk-LR; 10 mL). The mixture was concentrated under reduced pressure to remove traces of water. The procedure was repeated once more. and finally toluene (10 mL/g-bulk-LR; 10 mL). The system was inerted three times and stirred under nitrogen gas. 17:03:56: To the homogenous mixture was added 1-benzylpiperazine (1.3 eq; 0.852 g; 0.84 mL; 4.83 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.02 eq; 68 mg; 0.07 mmol), 2-(DI-T-BUTYLPHOSPHINO)BIPHE
The source
This record comes from experimental reaction archive (ord-3a55abb970674d2a9a710b323cb93eee). Open the source and check it against what is on this page.
experimental reaction archive record ord-3a55abb970674d2a9a710b323cb93eee 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.
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