Buchwald–Hartwig amination, record ord-1beac9199051463f81c658e8f7cb9a0d
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 | Tert-butyl 4-bromobenzoate | C₁₁H₁₃BrO₂ | |
| Reactant | Ethyl 4-piperidinecarboxylate | C₈H₁₅NO₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 1-(4-(tert-butoxycarbonyl)phenyl)piperidine-4-carboxylate | C₁₉H₂₇NO₄ | 0% |
Conditions
- Temperature
- 110 °C
Yield
- 0% of Ethyl 1-(4-(tert-butoxycarbonyl)phenyl)piperidine-4-carboxylate.
Procedure
Copied from the source record, unedited
1\. To a microwave tube was added tert-butyl 4-bromobenzoate (1.328 g, 5.16 mmol), ethyl piperidine-4-carboxylate (1.000 g, 5.16 mmol), Cs2CO3 (5.05 g, 15.49 mmol), Pd2dba3 (0.473 g, 0.52 mmol), and BINAP (0.643 g, 1.03 mmol). The mixture was dissolved in [Solvents] and sealed. The tube was de-gassed and inflated with N2. 2\. The reaction was heated at 110°C in oil-bath overnight. LCMS showed reaction complete. The reaction mixture was filter through celite pad and the solution was loaded to column for a ISCO purification (30% EtOAc in Hex). The purification is difficult with multiple by-products. Several ISCO purification was carried out and fractions were combined with other batches. Yield was poor.
The source
This record comes from experimental reaction archive (ord-1beac9199051463f81c658e8f7cb9a0d). Open the source and check it against what is on this page.
experimental reaction archive record ord-1beac9199051463f81c658e8f7cb9a0d 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.