Buchwald–Hartwig amination, record ord-1563c8430590422cb033c9d23b6239c7
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 | 1-Bromo-3,5-difluorobenzene | C₆H₃BrF₂ | |
| Reactant | N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide | C₂₀H₂₅N₃O₄ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide | C₂₆H₂₇F₂N₃O₄ | 51.21% |
Conditions
- Temperature
- 100 °C
Yield
- 51% of 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide.
Procedure
Copied from the source record, unedited
diacetoxypalladium (2.90 mg, 0.01 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (120 mg, 0.32 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (15.89 mg, 0.03 mmol), 1-bromo-3,5-difluorobenzene (46.5 µl, 0.40 mmol) and cesium carbonate (158 mg, 0.48 mmol) suspended in 1,4-dioxane (3184 µl). The resulting suspension was degased with argon and then stirred at 100 °C for 20 hours. The reaction mixture was allowed to cool to room temperature, The crude product was adsorbed on silica gel, the solvent was evaporated, and purified by flash chromatography on silica gel eluting with 0 to 10% methanol in ethyl acetate. The solvent was evaporated to dryness, the gum was triturated in Et2O/pentane to give a solid;
The source
This record comes from experimental reaction archive (ord-1563c8430590422cb033c9d23b6239c7). Open the source and check it against what is on this page.
experimental reaction archive record ord-1563c8430590422cb033c9d23b6239c7 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.