Buchwald–Hartwig amination, record ord-0d9db0bff06f4d53bf85fef23e44393c
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 | (S)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine | C₁₅H₁₅ClN₂O | |
| 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 | (S)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine | C₂₆H₂₇N₅O₂ | 27.89% |
Conditions
- Temperature
- 100 °C
Yield
- 28% of (S)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-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 (0.213 g, 0.89 mmol), Palladium(II) acetate (0.017 g, 0.07 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.026 g, 0.07 mmol) and Cesium carbonate (0.722 g, 2.22 mmol) were put in a 20 mL microwave vial and sealed. The vial was flushed with argon. (S)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.203 g, 0.74 mmol) in DME (5 mL) was added and additional 5 mL was added to the vial. The reaction mixture was run in the microwave at 100°C for 80 minutes. Reaction still not complete. Additional palladium(II)acetate (0.1 eq) and 2-(dicyclohexylphosphino)biphenyl (0.1 eq) were added and the reaction was run again in the microwave for 60 minutes. Have about 14% oxazepine left. Heated for additional 45 minutes. 10% oxazepine lef
The source
This record comes from experimental reaction archive (ord-0d9db0bff06f4d53bf85fef23e44393c). Open the source and check it against what is on this page.
experimental reaction archive record ord-0d9db0bff06f4d53bf85fef23e44393c 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.