Buchwald–Hartwig amination, record ord-57458b4fbe4c490eb3a4dddc522d1ef4
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 | 41.13% |
Conditions
- Temperature
- 100 °C
Yield
- 41% 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
8-chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one (173 mg, 0.60 mmol), 4-(2-methyl-1H-imidazol-1-yl)aniline (125 mg, 0.72 mmol), PdOAc2 (13.47 mg, 0.06 mmol), biphenyl-2-yldicyclohexylphosphine (21.03 mg, 0.06 mmol) and cesium carbonate (489 mg, 1.50 mmol) were placed in a microwave vial equipped with a stirring bar. The vial was capped, DME (4 mL) was added, the vial was flushed with nitrogen via a syringe and the mixture was heated to 100°C in a microwave reactor for 1 h. The residue was diluted with CH2Cl2 and filtered through a short plug of Celite. The filtrate was evaporated and the residue was purified by ISCO column chromatography on silica (gradient elution 0-6% methanol in dichloromethane) to give 4-methyl-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2-ph
The source
This record comes from experimental reaction archive (ord-57458b4fbe4c490eb3a4dddc522d1ef4). Open the source and check it against what is on this page.
experimental reaction archive record ord-57458b4fbe4c490eb3a4dddc522d1ef4 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.