Buchwald–Hartwig amination, record ord-cf737b8f3d9340aca6130b04f75e7c21
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 | 1,4-Dibromobenzene | C₆H₄Br₂ | |
| Reactant | 1-Piperazineacetic acid, methyl ester | C₇H₁₄N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Methyl 2-(4-(4-bromophenyl)piperazin-1-yl)acetate | C₁₃H₁₇BrN₂O₂ | 0% |
Conditions
- Temperature
- 85 °C
Yield
- 0% of Methyl 2-(4-(4-bromophenyl)piperazin-1-yl)acetate.
Procedure
Copied from the source record, unedited
In a reaction vial, 1,4-dibromobenzene (0.373 g, 1.58 mmol), methyl 2-(piperazin-1-yl)acetate (0.100 g, 0.63 mmol), CS2CO3 (0.309 g, 0.95 mmol), and BINAP (0.024 g, 0.04 mmol) were taken up in 1,4-dioxane (1.5 ml). Argon was bubbled through the solution for 1 minute. Pd2(dba)3 (0.012 g, 0.01 mmol) was added, followed by additional purging with argon. The vial was capped and placed on the heater-shaker. The reaction was stirred (450 rpm) at 100 °C overnight. LC/MS at this point did not indicate any formation of the dp. Experiment not progressed.
The source
This record comes from experimental reaction archive (ord-cf737b8f3d9340aca6130b04f75e7c21). Open the source and check it against what is on this page.
experimental reaction archive record ord-cf737b8f3d9340aca6130b04f75e7c21 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.