Buchwald–Hartwig amination, record ord-bc0ccb3ec3974a6197509c6aeefd5c4d
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 | Potassium Carbonate | CK₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Anisole | C₇H₈O | |
| Product | N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine | C₈H₆ClN₃O | 49.6% |
Conditions
- Temperature
- 120 °C
Yield
- 50% of N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine.
Procedure
Copied from the source record, unedited
Objective: Repeat of optimised conditions found in process research and devellopment screen for an isolated yield. An activated catalyst solution was prepared by adding TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (61.3 mg, 0.07 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (77 mg, 0.13 mmol) to an oven-dried microwave vial. The vial was then capped and purged with nitrogen and anisole (1 mL) (degassed) was added. The solution was stirred at 50°C for 40 mins, then 90°C for 15 mins (activated catalyst solution; Soln. 1). To another oven-dried microwave vial was added potassium carbonate (126 mg, 0.91 mmol), oxazol-2-amine (102 mg, 1.22 mmol) and 2,4-dichloropyridine (90 mg, 0.61 mmol) and the vial was capped and purged with nitrogen. anisole (1.35 mL) and the activated c
The source
This record comes from experimental reaction archive (ord-bc0ccb3ec3974a6197509c6aeefd5c4d). Open the source and check it against what is on this page.
experimental reaction archive record ord-bc0ccb3ec3974a6197509c6aeefd5c4d 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.