Buchwald–Hartwig amination, record ord-a21d6ec12c02473a98dce7de6b637849
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 | (R)-1-Boc-3-methylpiperazine | C₁₀H₂₀N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate | C₁₅H₂₃N₃O₂ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
diacetoxypalladium (9.34 mg, 0.04 mmol) and RuPhos (0.039 g, 0.08 mmol) were suspended in 1,4 dioxane (5 mL), degassed and stirred at 50 °C for 10 minutes. Then (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.100 g, 0.50 mmol), 3-bromopyridine (0.040 mL, 0.42 mmol) and cesium carbonate (0.203 g, 0.62 mmol) were added and the reaction mixture was stirred at 100 °C for 16 h. LCMS showed only 5% conversion to desired product. This was part of a screen and Ruphos, sodium tert-butoxide in toluene gave far better conversion so this was abandoned.
The source
This record comes from experimental reaction archive (ord-a21d6ec12c02473a98dce7de6b637849). Open the source and check it against what is on this page.
experimental reaction archive record ord-a21d6ec12c02473a98dce7de6b637849 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.