Buchwald–Hartwig amination, record ord-a7d27a030aca4653bd3b2b42172cb84b
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-methoxybenzamide | C₈H₁₀N₂O₂ | |
| 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)-4-pyridyl]amino]-N-methoxy-benzamide | C₁₉H₁₉F₃N₆O₂ | 74.87% |
Conditions
- Temperature
- 100 °C
Yield
- 75% of 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-N-methoxy-benzamide.
Procedure
Copied from the source record, unedited
(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.817 g, 3.14 mmol), diacetoxypalladium (0.353 g, 1.57 mmol), 2-amino-N-methoxybenzamide (8.87 g, 53.39 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (12 g, 31.40 mmol) and cesium carbonate (20.46 g, 62.81 mmol) were weighed out in a round bottom flask. dioxane (130 mL) was added and argon was let to bubble in the mixture for 10 minutes. The suspension was stirred at 100 °C overnight. 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. (Insolubles~19g). The crude product (30g) was purified by flash chromatography on silica gel eluting with 0 to 5
The source
This record comes from experimental reaction archive (ord-a7d27a030aca4653bd3b2b42172cb84b). Open the source and check it against what is on this page.
experimental reaction archive record ord-a7d27a030aca4653bd3b2b42172cb84b 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.