Buchwald–Hartwig amination, record ord-3db391e974974fdaa88ec87b15c89118
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 | 4-iodo-5-(trifluoromethyl)-N-(1,3,5-trimethylpyrazol-4-yl)pyridin-2-amine | C₁₂H₁₂F₃IN₄ | |
| Reactant | 2-Amino-N-methoxybenzamide | C₈H₁₀N₂O₂ | |
| 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 | N-methoxy-2-[[5-(trifluoromethyl)-2-[(1,3,5-trimethylpyrazol-4-yl)amino]pyridin-4-yl]amino]benzamide | C₂₀H₂₁F₃N₆O₂ | 89.15% |
Conditions
- Temperature
- 90 °C
Yield
- 89% of N-methoxy-2-[[5-(trifluoromethyl)-2-[(1,3,5-trimethylpyrazol-4-yl)amino]pyridin-4-yl]amino]benzamide.
Procedure
Copied from the source record, unedited
2-amino-N-methoxybenzamide (541 mg, 3.26 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (166 mg, 0.29 mmol), cesium carbonate (1249 mg, 3.83 mmol) and diacetoxypalladium (38.7 mg, 0.17 mmol) were added to a stirred solution of 4-iodo-5-(trifluoromethyl)-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)pyridin-2-amine (759 mg, 1.92 mmol) dissolved in dioxane (20 mL) in a µwave vial at RT. Argon was let to bubble in the mixture for 5 minutes and the resulting slurry was then stirred at 90 °C for 15 hours. Lcms showed complete reaction. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane, filtered, silica gel was added and the mixture was concentrated. The crude product was purified by flash chromatography on silica gel eluting with 30 to 100% ethyl
The source
This record comes from experimental reaction archive (ord-3db391e974974fdaa88ec87b15c89118). Open the source and check it against what is on this page.
experimental reaction archive record ord-3db391e974974fdaa88ec87b15c89118 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.