Buchwald–Hartwig amination, record ord-eba583eb36cf40e597f1d8a3b26c7756
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 | 8-Bromo-6-chloroimidazo(1,2-a)pyridine | C₇H₄BrClN₂ | |
| Reactant | 5-Morpholinopyridin-2-amine | C₉H₁₃N₃O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 6-chloro-N-(5-morpholinopyridin-2-yl)imidazo[1,2-a]pyridin-8-amine | C₁₆H₁₆ClN₅O | 65.27% |
Conditions
- Temperature
- 105 °C
Yield
- 65% of 6-chloro-N-(5-morpholinopyridin-2-yl)imidazo[1,2-a]pyridin-8-amine.
Procedure
Copied from the source record, unedited
A mixture of 8-bromo-6-chloroimidazo[1,2-a]pyridine, HCl (600mg, 2.24 mmol), 5-morpholinopyridin-2-amine (482 mg, 2.69 mmol), BINAP (279 mg, 0.45 mmol), cesium carbonate (1824 mg, 5.60 mmol) in Toluene (12 mL) was sparged with nitrogen while stirring for 10 minutes. palladium(II) acetate (87 mg, 0.39 mmol) was then added and the reaction stirred at 105 °C for overnight. At ths stage LC/MS indicated that formation of the product. After this time, the reaction was cooled to room temperature, diluted with mixture of 1:1 methanol/DCM ( 100 mL) and filtered through celite. The filtrated concentrated under reduced pressure and the resulting residue purified by flash chromatography (silicagel, 0-10% DCM/Methanol, 25 minutes) to afford 6-chloro-N-(5-morpholinopyridin-2-yl)imidazo[1,2-a]pyridin-8-a
The source
This record comes from experimental reaction archive (ord-eba583eb36cf40e597f1d8a3b26c7756). Open the source and check it against what is on this page.
experimental reaction archive record ord-eba583eb36cf40e597f1d8a3b26c7756 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.