Buchwald–Hartwig amination, record ord-124e8e40d3e54042af531dbb1d8d85d1
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 | 2-Bromo-4-chlorobenzonitrile | C₇H₃BrClN | |
| Reactant | Piperazine | C₄H₁₀N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-Chloro-2-(piperazin-1-yl)benzonitrile | C₁₁H₁₂ClN₃ | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of 4-Chloro-2-(piperazin-1-yl)benzonitrile.
Procedure
Copied from the source record, unedited
Tris(dibenzylideneacetone)dipalladium (0) (43.4 mg, 0.05 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (59.0 mg, 0.09 mmol) were added to a mixture of 2-bromo-4-chlorobenzonitrile (205 mg, 0.95 mmol), Cesium carbonate (463 mg, 1.42 mmol) and Piperazine (163 mg, 1.89 mmol) in dioxane (3 mL). Reaction vessel was placed in an oil bath set to 90 °C 2.45pm. LCMS o/n shows large product peak (222). Cooled, filtered through a silica plug, washing with EtOAc until filtrate is clear. Crude NMR is very messy, target deprioritized. Discarded.
The source
This record comes from experimental reaction archive (ord-124e8e40d3e54042af531dbb1d8d85d1). Open the source and check it against what is on this page.
experimental reaction archive record ord-124e8e40d3e54042af531dbb1d8d85d1 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.