Buchwald–Hartwig amination, record ord-3dc45e0d006e4925b34d5e9919e16fc1
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-chloro-1-ethoxybenzene | C₈H₈BrClO | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | CCOc1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1Cl | C₁₇H₂₅ClN₂O₃ | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of the product.
Procedure
Copied from the source record, unedited
In a 50 mL round-bottomed flask, PALLADIUM ACETATE (0.014 g, 0.06 mmol) was treated with BINAP (0.079 g, 0.13 mmol) under nitrogen in degassed Toluene (12.74 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 (0.237 g, 1.27 mmol), cesium carbonate (0.208 g, 0.64 mmol), potassium carbonate (0.176 g, 1.27 mmol), and 18-CROWN-6 (0.034 g, 0.13 mmol). The reaction was then treated with 4-bromo-2-chloro-1-ethoxybenzene (0.300 g, 1.27 mmol) and was allowed to stir at 80°C 5 h. **LCMS High pH:** No reaction observed
The source
This record comes from experimental reaction archive (ord-3dc45e0d006e4925b34d5e9919e16fc1). Open the source and check it against what is on this page.
experimental reaction archive record ord-3dc45e0d006e4925b34d5e9919e16fc1 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.