Buchwald–Hartwig amination: 8-Chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-F][1,4]oxazepin-5(2H)-one → 8-(4-Imidazol-1-ylanilino)-4-methyl-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5-one
38% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
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-(1H-imidazol-1-yl)aniline | C₉H₉N₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 8-(4-Imidazol-1-ylanilino)-4-methyl-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5-one | C₂₄H₂₁N₅O₂ | 37.83% |
Conditions
- Temperature
- 100 °C
Yield
- 38% of 8-(4-Imidazol-1-ylanilino)-4-methyl-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5-one.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
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 (115 mg, 0.40 mmol), 4-(1H-imidazol-1-yl)aniline (95 mg, 0.60 mmol), PdOAc2 (8.94 mg, 0.04 mmol), biphenyl-2-yldicyclohexylphosphine (13.96 mg, 0.04 mmol) and CS2CO3 (389 mg, 1.19 mmol) were placed in a microwave vial equipped with a stirring bar. The vial was capped and flushed with argon. DME (1.5 mL) was added via a syringe and the mixture was heated to 100°C in a microwave apparatus for 1 h. The residue was diluted with ethyl acetate and filtered through a short plug og Celite. The filtrate was evaporated and the residue was purified by HPLC to give 62 mg of the product as a solid.
The source
This record comes from experimental reaction archive (ord-b03de5e7ee154175b8ccb76d7202e229). Open the source and check it against what is on this page.
experimental reaction archive record ord-b03de5e7ee154175b8ccb76d7202e229 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.
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