Buchwald–Hartwig amination, record ord-c8bd9a8a68d6433daf2fe8e0bf9a22b5
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 | CNC(=O)c1ccc(F)cc1Nc1cc(Cl)ncc1C(F)(F)F | C₁₄H₁₀ClF₄N₃O | |
| Reactant | 1,3-Dimethyl-1H-pyrazol-5-amine | C₅H₉N₃ | |
| 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-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-4-fluoro-N-methyl-benzamide | C₁₉H₁₈F₄N₆O | 61.74% |
Conditions
- Temperature
- 90 °C
Yield
- 62% of 2-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-4-fluoro-N-methyl-benzamide.
Procedure
Copied from the source record, unedited
2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-4-fluoro-N-methylbenzamide (2 g, 5.75 mmol), 1,3-dimethyl-1H-pyrazol-5-amine (0.767 g, 6.90 mmol) diacetoxypalladium (0.103 g, 0.46 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.533 g, 0.92 mmol) and cesium carbonate (2.249 g, 6.90 mmol) were suspended in dioxane (25 ml). The reaction was degased, purged with argon (3 times) and heated to at 90 °C for 4 hours. The reaction mixture was allowed to cool to room temperature, diluted with DCM (some drop of MeOH) and filtered. Silica gel was added and solvents were evaporated to afford the crude, which was purified by flash chromatography on silica gel eluting with 0 to 10% methanol in ethyl acetate/DCM (1/1) . The solvent was evaporated to dryness to give a residue which wa
The source
This record comes from experimental reaction archive (ord-c8bd9a8a68d6433daf2fe8e0bf9a22b5). Open the source and check it against what is on this page.
experimental reaction archive record ord-c8bd9a8a68d6433daf2fe8e0bf9a22b5 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.