Buchwald–Hartwig amination, record ord-9e945d87965540af8be94a72eefc3798
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-2-cyclopropyl-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine | C₁₂H₁₅ClN₂O | |
| Reactant | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline | C₁₁H₁₃N₃O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 2-cyclopropyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine | C₂₃H₂₇N₅O₂ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 2-cyclopropyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine.
Procedure
Copied from the source record, unedited
3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.189 g, 0.93 mmol), 8-chloro-2-cyclopropyl-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.222 g, 0.93 mmol), Palladium acetate (0.021 g, 0.09 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.033 g, 0.09 mmol) and Cesium carbonate (0.303 g, 0.93 mmol) were added in a microwave vial. The mixture was capped and flushed with argon. 1,2-dimethoxyethane (2 mL) was added and the mixture was run in a microwave for 60 minutes at 100°C. Extremely little product was formed according to LCMS. Added 0.1 eq of Palladium acetate and 2-(Dicyclohexylphosphino)biphenyl and 1 eq Cesium carbonate and let run for another 60 min at 100°C in the microwave. According to LCMS ther is 13% startingmaterial oxazepine left. Added a small spatula of acetoxy(2'-(di-
The source
This record comes from experimental reaction archive (ord-9e945d87965540af8be94a72eefc3798). Open the source and check it against what is on this page.
experimental reaction archive record ord-9e945d87965540af8be94a72eefc3798 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.