Buchwald–Hartwig amination, record ord-1df95b34548d48fe94a49234436e46e5
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-Chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-F][1,4]oxazepin-5(2H)-one | C₁₅H₁₃ClN₂O₂ | |
| Reactant | 4-(2-methyl-1H-imidazol-1-yl)aniline | C₁₀H₁₁N₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 4-methyl-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one | C₂₅H₂₃N₅O₂ | 42.31% |
Conditions
- Temperature
- 100 °C
Yield
- 42% of 4-methyl-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one.
Procedure
Copied from the source record, unedited
were placed in a microwave vial equipped with a stirring bar. The vial was capped and flushed with argon. DME (2 mL) was added via a syringe and the mixture was heated to 100°C in a microwave apparatus for 1h. The reaction mixture was filtered, the solvent was evaporated and the residue was purified by HPLC to give 53 mg (42 % yield) of the product as a solid.
The source
This record comes from experimental reaction archive (ord-1df95b34548d48fe94a49234436e46e5). Open the source and check it against what is on this page.
experimental reaction archive record ord-1df95b34548d48fe94a49234436e46e5 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.