Buchwald–Hartwig amination: 3-Bromopyridine → 1-(Pyridin-3-yl)piperazine
0% yield, run at 130 °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 | 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.
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.
- tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate103%
- tert-butyl N-[2-chloro-5-(piperazin-1-yl)phenyl]carbamate57%
- 4-(2-Fluoro-4-methylphenylamino)-7-(piperazin-1-yl)cinnoline-3-carbonitrile51%
- N-(Pyridin-3-yl)pyridin-2-amine22%
- (4-Cyclobutylpiperazin-1-yl)-(7-pyridin-3-yl-7-azaspiro[3.5]nonan-2-yl)methanone8%
- N-pyridin-3-ylbenzamidenot recorded
- 5-phenyl-N-pyridin-3-ylpyridin-2-aminenot recorded
- 2-phenyl-N'-pyridin-3-ylethanimidamidenot recorded
- 3-Pyridinamine, N-(4-methylphenyl)-99%
- 3-Pyridinamine, N-(4-methylphenyl)-98%
- 3-Pyridinamine, N-(4-methylphenyl)-95%
- 3-Pyridinamine, N-(4-methylphenyl)-95%
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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.