Buchwald–Hartwig amination, record ord-7696589313724974b3ed4cfa26a52287
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-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine | C₁₁H₁₀F₃IN₄ | |
| Reactant | 2-amino-4-fluoro-N-methylbenzamide | C₈H₉FN₂O | |
| 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 | 36.19% |
Conditions
- Temperature
- 100 °C
Yield
- 36% 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-amino-4-fluoro-N-methylbenzamide (2.310 g, 13.74 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (3.5 g, 9.16 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.530 g, 0.92 mmol) diacetoxypalladium (0.103 g, 0.46 mmol) and cesium carbonate (5.97 g, 18.32 mmol) were suspended in dioxane (40 mL). The reaction was degased, purged with argon (3 times) and heated to 100 °C for 5 hours. The reaction mixture was allowed to cool to room temperature under stirring, diluted with ethyl acetate and the insolubles were removed by filtration, washed with EtOAc and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% methanol in ethyl acetate/DCM (1/1). Fractions containing pure prod
The source
This record comes from experimental reaction archive (ord-7696589313724974b3ed4cfa26a52287). Open the source and check it against what is on this page.
experimental reaction archive record ord-7696589313724974b3ed4cfa26a52287 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.