Buchwald–Hartwig amination: 7-Bromo-N,N-dimethyl-benzofuran-2-carboxamide → 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide
52% 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 | 7-Bromo-N,N-dimethyl-benzofuran-2-carboxamide | C₁₁H₁₀BrNO₂ | |
| Reactant | 1-Benzylpiperazine | C₁₁H₁₆N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide | C₂₂H₂₅N₃O₂ | 52.15% |
Conditions
- Temperature
- 95 °C
Yield
- 52% of 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide.
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.
- 1-Benzyl-4-(4-fluorophenyl)piperazine75%
- 8-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester48%
- Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate27%
- Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate0%
- Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate0%
Procedure
Copied from the source record, unedited
The mixture of Tris(dibenzylideneacetone)dipalladium(0) (0.222 g, 0.24 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.231 g, 0.48 mmol) in dioxane (10 mL) (degassed with argon for 5 min) was heated at 95 °C under argon for 5 min . This was transferred to a flask containing 7-bromo-N,N-dimethylbenzofuran-2-carboxamide (1.3 g, 4.85 mmol), 1-benzylpiperazine (1.111 g, 6.30 mmol) and Cesium carbonate (2.212 g, 6.79 mmol) in dioxane (10 mL) (degassed with argon for 5 min). The resulting mixture was heated at 95 °C over night. After cooling, the reaction mixture was filtered, the solid washed with DCM and concentrated. The product was purified by isco (DCM:MeOH; 0-3%). A small portion was also purified by prepLC giving EN02745-79-002.
The source
This record comes from experimental reaction archive (ord-f1c56ffe105843279dcf3ce82ed9a4b2). Open the source and check it against what is on this page.
experimental reaction archive record ord-f1c56ffe105843279dcf3ce82ed9a4b2 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.
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