Buchwald–Hartwig amination, record ord-80eaa5d6e27d4cf78d75715b3843cadc
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 | 4-Bromo-2-chlorobenzonitrile | C₇H₃BrClN | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Tert-butyl 4-(3-chloro-4-cyanophenyl)piperazine-1-carboxylate | C₁₆H₂₀ClN₃O₂ | 47.09% |
Conditions
- Temperature
- 80 °C
Yield
- 47% of Tert-butyl 4-(3-chloro-4-cyanophenyl)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
In a 250 mL round-bottomed dried flask , diacetoxypalladium (0.036 g, 0.16 mmol) was treated with 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.195 g, 0.31 mmol) under nitrogen in toluene (35 mL). The reaction was heated to 80 °C and was stirred for 10 min. To the flask was then added tert-butyl piperazine-1-carboxylate (0.602 g, 3.23 mmol), cesium carbonate (0.527 g, 1.62 mmol), potassium carbonate (0.447 g, 3.23 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (0.085 g, 0.32 mmol). The reaction was then treated with 4-bromo-2-chlorobenzonitrile (0.7 g, 3.23 mmol) and was allowed to stir at 80°C for 5 h. The mixture was then filtered over celite and celite was washed with heptanes. The mixture was condensed under reduced pressure and the crude material was purified on preparative HPLC MS
The source
This record comes from experimental reaction archive (ord-80eaa5d6e27d4cf78d75715b3843cadc). Open the source and check it against what is on this page.
experimental reaction archive record ord-80eaa5d6e27d4cf78d75715b3843cadc 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.