Buchwald–Hartwig amination, record ord-cdacdc2f62e2433897c344ea48603986
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 | 2-Chloropyridine | C₅H₄ClN | |
| Reactant | 2-Aminooxazole | C₃H₄N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N-pyridin-2-yl-1,3-oxazol-2-amine | C₈H₇N₃O | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of N-pyridin-2-yl-1,3-oxazol-2-amine.
Procedure
Copied from the source record, unedited
Palladium(II) acetate (4.49 mg, 0.02 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.017 g, 0.03 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Dioxane (1 mL) was added and the resulting mixture was heated to to 50°C for 30 minutes. oxazol-2-amine (0.101 g, 1.20 mmol) together with 2-chloropyridine (0.094 mL, 1.00 mmol) and cesium carbonate (0.456 g, 1.40 mmol) were placed in a second vessel, evacuated and purged with nitrogen 3 times and dioxane (3 mL) was added. The catalyst solution was added and the resulting mixture heated at 100 °C for 16 hours. **No oxazol-2-amine present in proton NMR of crude reaction mixture.** The starting material is decomposing under the reaction conditions, could be the route of the very low prod
The source
This record comes from experimental reaction archive (ord-cdacdc2f62e2433897c344ea48603986). Open the source and check it against what is on this page.
experimental reaction archive record ord-cdacdc2f62e2433897c344ea48603986 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.