Buchwald–Hartwig amination, record ord-6df914594aae4a42ba5b1bcb65424482
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-4,6-dimethyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine | C₁₂H₁₄ClF₃N₂O | |
| Reactant | 5-(4-Methyl-1H-imidazol-1-yl)pyridin-2-amine | C₉H₁₀N₄ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 4,6-Dimethyl-N-(5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine | C₂₁H₂₃F₃N₆O | 15.45% |
Conditions
- Temperature
- 110 °C
Yield
- 15% of 4,6-Dimethyl-N-(5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine.
Procedure
Copied from the source record, unedited
To 8-chloro-4,6-dimethyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (300 mg, 0.51 mmol) in DME (4 mL) were 5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (89 mg, 0.51 mmol), cesium carbonate (249 mg, 0.76 mmol), 2-(Dicyclohexylphosphino)biphenyl (17.84 mg, 0.05 mmol) and Palladium acetate (11.43 mg, 0.05 mmol) added. The reaction was heated to 110°C for 3*90min. The solids were filtered of and washed with DCM and IPA and discarded. The solvents were evaporated and the crude product was purified using first flash chromatography, 0-7% MeOH in DCM and the prepHPLC yielding 4,6-dimethyl-N-(5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (34.0 mg, 15.45 %)
The source
This record comes from experimental reaction archive (ord-6df914594aae4a42ba5b1bcb65424482). Open the source and check it against what is on this page.
experimental reaction archive record ord-6df914594aae4a42ba5b1bcb65424482 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.