Buchwald–Hartwig amination, record ord-c9d3e32c4ae3434fab0938e5982b9ebd
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 | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate | C₁₄H₂₁N₃O₂ | 37.96% |
Conditions
- Temperature
- 100 °C
Yield
- 38% of Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
diacetoxypalladium (0.072 g, 0.32 mmol) and RuPhos (0.301 g, 0.64 mmol) were stirred in 1,4-dioxane (11.36 ml) for 10 mins at 50 °C.tert-butyl piperazine-1-carboxylate (0.6 g, 3.22 mmol), 3-bromopyridine (0.310 ml, 3.22 mmol) and sodium tert-butoxide (0.464 g, 4.83 mmol) were added and the reaction mixture was stirred at 100 °C for 64 h. The reaction mixture was filtered through celite. The crude product was purified by flash silica chromatography, elution gradient 20 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(pyridin-3-yl)piperazine-1-carboxylate (0.322 g, 38.0 %) as a yellow oil which crystallised on standing. This was then combined with EN06111-39-01.
The source
This record comes from experimental reaction archive (ord-c9d3e32c4ae3434fab0938e5982b9ebd). Open the source and check it against what is on this page.
experimental reaction archive record ord-c9d3e32c4ae3434fab0938e5982b9ebd 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.