Buchwald–Hartwig amination: N-(1,3-dimethylpyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine → 2-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N,6-dimethoxybenzamide
0% yield, run at 90 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
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,6-dimethoxybenzamide | C₉H₁₂N₂O₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| 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,6-dimethoxybenzamide | C₂₀H₂₁F₃N₆O₃ | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of 2-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N,6-dimethoxybenzamide.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 90 °C | — | 72% |
| Binap, (A+-)-; Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 90 °C | — | 0% (this run) |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Potassium Carbonate | 1,4-Dioxane | 90 °C | — | 0% |
Procedure
Copied from the source record, unedited
N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), 2-amino-N,6-dimethoxybenzamide (43.6 mg, 0.22 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (8.15 mg, 0.01 mmol) and cesium carbonate (85 mg, 0.26 mmol) were suspended in 1,4-dioxane (436 µl) and sealed into a microwave tube. The reaction was degased, purged with nitrogen and heated to 90 °C overnight => _slow reaction, a few expected product formed, no des-iodo observed, both SM left_ **_NOT ISOLATED_**
The source
This record comes from experimental reaction archive (ord-172edbc585f4482992d8b345126c6340). Open the source and check it against what is on this page.
experimental reaction archive record ord-172edbc585f4482992d8b345126c6340 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.