Buchwald–Hartwig amination, record ord-91c1aa5c02fc46a586e9f5a373b7526a
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-fluorobenzonitrile | C₇H₃BrFN | |
| Reactant | Piperazine | C₄H₁₀N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-Fluoro-2-(piperazin-1-yl)benzonitrile | C₁₁H₁₂FN₃ | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of 4-Fluoro-2-(piperazin-1-yl)benzonitrile.
Procedure
Copied from the source record, unedited
Tris(dibenzylideneacetone)dipalladium (0) (57.2 mg, 0.06 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (78 mg, 0.12 mmol) were added to a mixture of 2-bromo-4-fluorobenzonitrile (250 mg, 1.25 mmol), Cesium carbonate (611 mg, 1.87 mmol) and Piperazine (215 mg, 2.50 mmol) in dioxane (3 mL). Reaction vessel was placed in an oil bath at 90 °C 4pm. LCMS o/n shows several peaks. Larger peak corresponding to displacement of F by piperazine (MW266) than for desired product (205). Discarded
The source
This record comes from experimental reaction archive (ord-91c1aa5c02fc46a586e9f5a373b7526a). Open the source and check it against what is on this page.
experimental reaction archive record ord-91c1aa5c02fc46a586e9f5a373b7526a 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.