Buchwald–Hartwig amination, record ord-18cf4521e927457b894e96f153aedd6a
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-Chloro-5-(trifluoromethyl)pyridine | C₆H₃ClF₃N | |
| Reactant | Ethyl 2-amino-1,3-oxazole-5-carboxylate | C₆H₈N₂O₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 2-[[5-(trifluoromethyl)-2-pyridinyl]amino]-1,3-oxazole-5-carboxylate | C₁₂H₁₀F₃N₃O₃ | 61.47% |
Conditions
- Temperature
- 160 °C
Yield
- 61% of Ethyl 2-[[5-(trifluoromethyl)-2-pyridinyl]amino]-1,3-oxazole-5-carboxylate.
Procedure
Copied from the source record, unedited
Objective: Test of scope in the coupling of ester substituted aminooxazole To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), 2-chloro-5-(trifluoromethyl)pyridine (181 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.075 mmol) and the vial was capped and purged with nitrogen. dioxane (4 mL) (degassed) was added and the reaction mixture was heated to 160 °C for 1 h under microwave irradiation. LCMS of the crude reaction mixture indicated that the desired product had been formed with very small amounts of side products apparent. DCM (20 mL) was added to the crude reaction mixture together with silica (2
The source
This record comes from experimental reaction archive (ord-18cf4521e927457b894e96f153aedd6a). Open the source and check it against what is on this page.
experimental reaction archive record ord-18cf4521e927457b894e96f153aedd6a 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.