Buchwald–Hartwig amination, record ord-de391e2f60334b77bfa7be520f63a36b
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 | 2,4-Dichloropyridine | C₅H₃Cl₂N | |
| Reactant | 2-Aminooxazole | C₃H₄N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Bis(3,5-bis(trifluoromethyl)phenyl)(3,6-dimethoxy-2',4',6'-tri(propan-2-yl)(1,1'-biphenyl)-2-yl)phosphane | C₃₉H₃₇F₁₂O₂P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine | C₈H₆ClN₃O | 0% |
Conditions
- Temperature
- 140 °C
Yield
- 0% of N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine.
Procedure
Copied from the source record, unedited
Objective: Reactions using ligands not previously tested under these conditions 2,4-dichloropyridine (0.109 mL, 1.01 mmol), oxazol-2-amine (85 mg, 1.01 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (23.20 mg, 0.03 mmol), bis(3,5-bis(trifluoromethyl)phenyl)(2',4',6'-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (81 mg, 0.10 mmol) and cesium carbonate (660 mg, 2.03 mmol) were added to an oven-dried microwave vail and the vial was purged with nitrogen. Degassed dioxane (4mL) was then added and the reaction mixture was heated to 140 °C for 1 h under microwave irradiation. Conclusion: None of the desired product was observed in the LCMS of the crude reaction mixture, not progressed.
The source
This record comes from experimental reaction archive (ord-de391e2f60334b77bfa7be520f63a36b). Open the source and check it against what is on this page.
experimental reaction archive record ord-de391e2f60334b77bfa7be520f63a36b 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.