Buchwald–Hartwig amination, record ord-dc56e46e611f4db1889616d29baeeb5f
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 4-Bromo-1-benzofuran-2-carboxamide | C₉H₆BrNO₂ | |
| Reactant | Piperazine | C₄H₁₀N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Tetrahydrofuran | C₄H₈O | |
| Product | 4-Piperazin-1-yl-1-benzofuran-2-carboxamide | C₁₃H₁₅N₃O₂ | 0% |
Conditions
- Temperature
- 70 °C
Yield
- 0% of 4-Piperazin-1-yl-1-benzofuran-2-carboxamide.
Procedure
Copied from the source record, unedited
The crude product from EN03731-54-001, 4-bromobenzofuran-2-carboxamide (0.600 g, 2.5 mmol), was dissolved in THF (18 mL) and water (18.00 mL). To this mixture were added piperazine (1.077 g, 12.50 mmol), Cesium carbonate (1.629 g, 5.00 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.114 g, 0.13 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.156 g, 0.25 mmol) and the reaction was heated at 70 °C over night. 2010-04-13 No product was detected. The reaction mixture was filtered and solvents were removed in vacuo. The residue was partitioned between methylene chloride and water. The organic layer was washed with 1M HCl(aq), dired with sodium sulfate, filtered, concentrated and purified by flash chromatography(Isolute Si 70g, methylene chloride: methanol; 97:3). No product cou
The source
This record comes from experimental reaction archive (ord-dc56e46e611f4db1889616d29baeeb5f). Open the source and check it against what is on this page.
experimental reaction archive record ord-dc56e46e611f4db1889616d29baeeb5f 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.