Buchwald–Hartwig amination, record ord-ea73803169b640e3b40a2b6127b91b44
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-(2,5-Dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine | C₁₁H₆Cl₂N₄ | |
| Reactant | 1-(4-(4-Amino-2,5-dimethoxyphenyl)piperazin-1-yl)ethanone | C₁₄H₂₁N₃O₃ | |
| 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 | 1-[4-[4-[(5-Chloro-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]-2,5-dimethoxyphenyl]piperazin-1-yl]ethanone | C₂₅H₂₆ClN₇O₃ | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of 1-[4-[4-[(5-Chloro-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]-2,5-dimethoxyphenyl]piperazin-1-yl]ethanone.
Procedure
Copied from the source record, unedited
_3-(2,5-dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine (132.5 mg, 0.50 mmol)_ _ _ _1-(4-(4-amino-2,5-dimethoxyphenyl)piperazin-1-yl)ethanone (140 mg, 0.50 mmol)_ ___(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (23.14 mg, 0.04 mmol)_ _ _ _cesium carbonate (244 mg, 0.75 mmol)_ ___diacetoxypalladium (4.49 mg, 0.02 mmol)_ _were suspended in_ _1,4-dioxane (4 ml)_ _,degased with argon . The mixture was heated to_ _80 °C_ _ for 2 hrs *_
The source
This record comes from experimental reaction archive (ord-ea73803169b640e3b40a2b6127b91b44). Open the source and check it against what is on this page.
experimental reaction archive record ord-ea73803169b640e3b40a2b6127b91b44 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.