Buchwald–Hartwig amination, record ord-43f679e964f04e22b49e850c529e3849
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 | 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-(pyridin-2-ylamino)-1,3-oxazole-5-carboxylate | C₁₁H₁₁N₃O₃ | 37.77% |
Conditions
- Temperature
- 160 °C
Yield
- 38% of Ethyl 2-(pyridin-2-ylamino)-1,3-oxazole-5-carboxylate.
Procedure
Copied from the source record, unedited
Objective: To test the substrate scope in 5-ester substituted 2-aminooxazole coupling. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.075 mmol), cesium carbonate (651 mg, 2.00 mmol), ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol) and 2-chloropyridine (113 mg, 1.00 mmol) were placed in an oven dried microwave vial. The vial was then capped and placed under an inert atmosphere. Dioxane (4 mL) was added and the mixture was heated to 160 °C for 1 h under microwave irradiation. LCMS of the crude reaction mixture indicated the presence of the desired product. DCM (10 mL) was added to the crude reaction mixture together with C-18 silica (2 g), and the solvent was removed under reduced pressure. The so
The source
This record comes from experimental reaction archive (ord-43f679e964f04e22b49e850c529e3849). Open the source and check it against what is on this page.
experimental reaction archive record ord-43f679e964f04e22b49e850c529e3849 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.