Buchwald–Hartwig amination, record ord-0f54af454e1c49e3950d93f112c4112b
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-6-methoxy-N-methylbenzamide | C₉H₁₂N₂O₂ | |
| 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-dimethyl-1H-pyrazol-5-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide | C₂₀H₂₁F₃N₆O₂ | 45.95% |
Conditions
- Temperature
- 100 °C
Yield
- 46% of 2-(2-(1,3-dimethyl-1H-pyrazol-5-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide.
Procedure
Copied from the source record, unedited
A suspension of 2-amino-6-methoxy-N-methylbenzamide (8.84 g, 49.07 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (12.5 g, 32.71 mmol), diacetoxypalladium (0.367 g, 1.64 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.893 g, 3.27 mmol) and cesium carbonate (19.18 g, 58.88 mmol) in dioxane (130 mL) was degassed with argon, which was also let to bubble for 10 minutes then stirred at reflux for 6h. The reaction mixture was allowed to cool to rt, the insolubles were removed by filtration, washed with EtOAc and the filtrate was concentrated. (Insolubles~23g). The crude product (20g) was purified by flash chromatography on silica gel eluting with 0 to 5% methanol in ethyl acetate. The solvent was evaporated to dryness to afford a foam (7.9g
The source
This record comes from experimental reaction archive (ord-0f54af454e1c49e3950d93f112c4112b). Open the source and check it against what is on this page.
experimental reaction archive record ord-0f54af454e1c49e3950d93f112c4112b 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.