Buchwald–Hartwig amination: 2-Chloropyridine → N-pyridin-2-yl-1,3-oxazol-2-amine
0% yield, run at 90 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-Chloropyridine | C₅H₄ClN | |
| Reactant | 2-Aminooxazole | C₃H₄N₂O | |
| Reagent | Potassium Carbonate | CK₂O₃ | |
| Catalyst | 2-(di-tert-butylphosphino)-N-phenylindole | C₂₂H₂₈NP | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N-pyridin-2-yl-1,3-oxazol-2-amine | C₈H₇N₃O | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of N-pyridin-2-yl-1,3-oxazol-2-amine.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 100 °C | — | 0% |
| 2-(di-tert-butylphosphino)-N-phenylindole; Bis(dibenzylideneacetone)palladium | Potassium Carbonate | 1,4-Dioxane | 90 °C | — | 0% (this run) |
| Brettphos; Bis(dibenzylideneacetone)palladium | Potassium Carbonate | 1,4-Dioxane | 90 °C | — | 0% |
Procedure
Copied from the source record, unedited
Objective: Comparison of the reactivity of 2-aminooxazole in the coupling with 2-chloropyridine using three different catalyst systems ( previously shown to be the best performers in a 96-well Process Research and Development Screen) To an oven-dried microwave vial was added TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) and 2-(di-tert- butylphosphino)-1-phenyl-1H-indole (0.067 g, 0.2 mmol) and the vial was purged with nitrogen. dioxane (2 mL) (degassed) was added and the reaction mixture was heated to 50 °C for 40 min followed by heating to 90 °C for a further 15 min (Solution 1). To an oven dried microwave vial was added 2-chloropyridine (0.095 mL, 1 mmol), oxazol-2-amine (0.187 g, 2.00 mmol), potassium carbonate (0.207 g, 1.50 mmol) and 4,4'-di-tert-butylbiphenyl (0.0
The source
This record comes from experimental reaction archive (ord-05c9f5ab86694790884a2465aacb6f95). Open the source and check it against what is on this page.
experimental reaction archive record ord-05c9f5ab86694790884a2465aacb6f95 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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