Buchwald–Hartwig amination, record ord-a6f7db18dd5949e09df857ba4df0f8b1
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 | 5-Bromo-2,2-difluoro-1,3-benzodioxole | C₇H₃BrF₂O₂ | |
| Reactant | Piperazine | C₄H₁₀N₂ | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | Tris(1,1-dimethylethyl)phosphine | C₁₂H₂₇P | |
| Catalyst | Bis(tri-tert-butylphosphine)palladium(0) | C₂₄H₅₄P₂Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 1-(2,2-Difluoro-2H-1,3-benzodioxol-5-YL)piperazine | C₁₁H₁₂F₂N₂O₂ | 50.68% |
Conditions
- Temperature
- 90 °C
Yield
- 51% of 1-(2,2-Difluoro-2H-1,3-benzodioxol-5-YL)piperazine.
Procedure
Copied from the source record, unedited
13-May-09 10:32:07 +0100 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (0.500 g, 2.11 mmol), piperazine (0.182 g, 2.11 mmol) and BIS(TRI-T-BUTYLPHOSPHINE)PALLADIUM(0) (0.054 g, 0.11 mmol) and potassium 2-methylpropan-2-olate (0.349 g, 2.95 mmol) were suspended in dioxane (10vol) (10 mL) and heated to 90°C for 1 hour. LC-MS shows no starting material 52% product and 41% dimer. The reaction mixture was combined with EN02263-54 filtered and the crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)piperazine (0.259 g, 50.7 %) as a yellow oil.
The source
This record comes from experimental reaction archive (ord-a6f7db18dd5949e09df857ba4df0f8b1). Open the source and check it against what is on this page.
experimental reaction archive record ord-a6f7db18dd5949e09df857ba4df0f8b1 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.