Buchwald–Hartwig amination, record ord-84fa8d5c5cab44cab16622511b581f38
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-N-(2-hydroxyethoxy)benzamide | C₉H₁₂N₂O₃ | |
| 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)pyridin-4-yl]amino]-N-(2-hydroxyethoxy)benzamide | C₂₀H₂₁F₃N₆O₃ | 48.64% |
Conditions
- Temperature
- 90 °C
Yield
- 49% of 2-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N-(2-hydroxyethoxy)benzamide.
Procedure
Copied from the source record, unedited
(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (22.71 mg, 0.04 mmol), diacetoxypalladium (4.41 mg, 0.02 mmol), 2-amino-N-(2-hydroxyethoxy)benzamide (131 mg, 0.67 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol) and cesium carbonate (256 mg, 0.79 mmol) were weighed out in a µwave vial, sealed and dioxane (4 mL) was added. Reaction was degassed with nitrogen. The reaction was stirred at 90 °C for 12 hours => _incomplete (~85% conversion)_. A few Pd(OAc)2, Xantphos and Cs2CO3 were added. Reaction was degassed with nitrogen and stirred at 90°C for 2 hours => _almost complete._ The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane and MeOH and silica (40-63 µm) was added. Mixture was concentrate
The source
This record comes from experimental reaction archive (ord-84fa8d5c5cab44cab16622511b581f38). Open the source and check it against what is on this page.
experimental reaction archive record ord-84fa8d5c5cab44cab16622511b581f38 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.