Buchwald–Hartwig amination, record ord-7137664b914247a99384dbf76411ea05
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 | Ethyl 6-chloronicotinate | C₈H₈ClNO₂ | |
| 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-ethoxycarbonyl-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate | C₁₄H₁₅N₃O₅ | 67.21% |
Conditions
- Temperature
- 160 °C
Yield
- 67% of Ethyl 2-[(5-ethoxycarbonyl-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), 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. ethyl 6-chloronicotinate (185 mg, 1.00 mmol) and dioxane (4 mL) (degassed) were 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 formed with minimal formation of side-products. DCM (20 mL) was added to the crude reaction mixture together with silica (2 g). The solvent was re
The source
This record comes from experimental reaction archive (ord-7137664b914247a99384dbf76411ea05). Open the source and check it against what is on this page.
experimental reaction archive record ord-7137664b914247a99384dbf76411ea05 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.