Buchwald–Hartwig amination, record ord-5ee406d12bbe4c6fbfb323cf21dcbb47
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 | 3-Bromopyridine | C₅H₄BrN | |
| Reactant | Piperazine | C₄H₁₀N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Tris(1,1-dimethylethyl)phosphine | C₁₂H₂₇P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | P-Xylene | C₈H₁₀ | |
| Product | 1-(Pyridin-3-yl)piperazine | C₉H₁₃N₃ | 0% |
Conditions
- Temperature
- 130 °C
Yield
- 0% of 1-(Pyridin-3-yl)piperazine.
Procedure
Copied from the source record, unedited
In a 100 ml RBF, 3-bromopyridine (1.220 mL, 12.66 mmol) was taken in xylenes (20 mL). To this was added tris(dibenzylideneacetone)dipalladium(0) (0.232 g, 0.25 mmol), tri-t-butylphosphine (10%wt in Hexane) (1.281 g, 0.63 mmol) and sodium tert-butoxide (1.825 g, 18.99 mmol). Then piperazine (6.54 g, 75.95 mmol) was added to RM and the RM was then heated at 130 °C for 5 hrs. The reaction was monitored by LCMS. It did not show formation of product. The RM was discarded.
The source
This record comes from experimental reaction archive (ord-5ee406d12bbe4c6fbfb323cf21dcbb47). Open the source and check it against what is on this page.
experimental reaction archive record ord-5ee406d12bbe4c6fbfb323cf21dcbb47 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.