Buchwald–Hartwig amination, record ord-5dfaf464504c42b7bafec75259e5a214
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 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine | C₈H₆ClN₃O | 11.1% |
Conditions
- Temperature
- 100 °C
Yield
- 11% of N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine.
Procedure
Copied from the source record, unedited
Palladium(II) acetate (11.38 mg, 0.05 mmol) was added in a single portion to a degassed solution of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (44.0 mg, 0.08 mmol), oxazol-2-amine (85 mg, 1.01 mmol), cesium carbonate (768 mg, 2.36 mmol),2,4-dichloropyridine (0.109 mL, 1.01 mmol), dioxane (4 mL) and DMSO (0.8 mL) and the resulting mixture was heated at 100 °C for 16 hours under a nitrogen atmosphere. Note: the reaction mixture was degassed by first combing the reagents (with the exception of Pd((OAc)2), sealing the vessel and carrying out three pump- purge cycles (vac-nitrogen). Dioxane was then added to this mixture via syringe, followed by the Pd(OAc)2 in a single portion and the vessel was heated for the required time as above. Solvent boiled dry from reaction overnight. Only DMSO
The source
This record comes from experimental reaction archive (ord-5dfaf464504c42b7bafec75259e5a214). Open the source and check it against what is on this page.
experimental reaction archive record ord-5dfaf464504c42b7bafec75259e5a214 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.