Buchwald–Hartwig amination, record ord-9c57f3e17c814398b6e1a1b710de4610
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 | 3-Amino-5-bromopyridine | C₅H₅BrN₂ | |
| Reactant | Morpholine | C₄H₉NO | |
| 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 | 5-Morpholinopyridin-3-amine | C₉H₁₃N₃O | 0% |
Conditions
- Temperature
- 150 °C
Yield
- 0% of 5-Morpholinopyridin-3-amine.
Procedure
Copied from the source record, unedited
diacetoxypalladium (20.76 mg, 0.09 mmol) was added to 5-bromopyridin-3-amine (160 mg, 0.92 mmol), morpholine (4028 µl, 46.24 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (64.2 mg, 0.11 mmol) and cesium carbonate (603 mg, 1.85 mmol). The resulting suspension was stirred at 150 °C for 30 minutes in a microwave. Reaction very messy but some product is visible. Reaction abandoned.
The source
This record comes from experimental reaction archive (ord-9c57f3e17c814398b6e1a1b710de4610). Open the source and check it against what is on this page.
experimental reaction archive record ord-9c57f3e17c814398b6e1a1b710de4610 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.