Buchwald–Hartwig amination, record ord-13cef69f8e724020954e5476c0d66794
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 | 2,6-Dibromopyridine | C₅H₃Br₂N | |
| Reactant | 4-Aminotetrahydropyran | C₅H₁₁NO | |
| 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 | 6-Bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine | C₁₀H₁₃BrN₂O | 0% |
Conditions
Yield
- 0% of 6-Bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine.
Procedure
Copied from the source record, unedited
to 2,6-dibromopyridine (100 mg, 0.42 mmol), 4-Aminotetrahydropyran (42.7 mg, 0.42 mmol) in dioxane (3 mL) while bubbling N2 was added Xantphos (24.43 mg, 0.04 mmol), CS2CO3 (316 mg, 0.97 mmol) and palladium(II) acetate (9.48 mg, 0.04 mmol). This was heated in a microwave at 130 oC for 30 mins. A small peak corresponding to product was obseved. Discontinued
The source
This record comes from experimental reaction archive (ord-13cef69f8e724020954e5476c0d66794). Open the source and check it against what is on this page.
experimental reaction archive record ord-13cef69f8e724020954e5476c0d66794 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.