Buchwald–Hartwig amination: Tert-butyl 4-bromobenzoate → Ethyl 1-(4-(tert-butoxycarbonyl)phenyl)piperidine-4-carboxylate
0% yield, run at 110 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
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.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
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.
Where to next
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