Buchwald–Hartwig amination, record ord-ec30b6a8454048268e227104fe1b995b
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 | N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine | C₁₁H₁₀F₃IN₄ | |
| Reactant | 2-Amino-N-methylbenzamide | C₈H₁₀N₂O | |
| 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 | 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N-methylbenzamide | C₁₉H₁₉F₃N₆O | 94.49% |
Conditions
- Temperature
- 90 °C
Yield
- 94% of 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N-methylbenzamide.
Procedure
Copied from the source record, unedited
2-amino-N-methylbenzamide (39.3 mg, 0.26 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.57 mg, 0.01 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol) and cesium carbonate (85 mg, 0.26 mmol) were dissolved in dioxane (1 mL) and sealed into a microwave tube. Argon was let to bubble in the mixture for 5 minutes. The reaction was heated to 90 °C, over a period of 90 minutes. LCMS showed complete and pretty clean reaction. The reaction mixture was allowed to cool to room temperature under stirring, diluted with dichloromethane and decalite speed + was added. The mixture was concentrated and the crude product was purified by flash chromatography on silica gel eluting with 0 to 5% met
The source
This record comes from experimental reaction archive (ord-ec30b6a8454048268e227104fe1b995b). Open the source and check it against what is on this page.
experimental reaction archive record ord-ec30b6a8454048268e227104fe1b995b 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.