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 | Potassium Carbonate | CK₂O₃ | |
| 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,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% |
| 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% (this run) |
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), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.57 mg, 0.01 mmol) and potassium carbonate (36.2 mg, 0.26 mmol) were suspended in 1,4-dioxane (423 µl) and sealed into a microwave tube. The reaction was degased, purged with nitrogen and heated to 90 °C overnight => _not complete but seemed to be clean, no des-iodo by-product formed, both SM left_ Same reaction was performed in toluene (423 µl) => _reaction complete, LCMS profile similar to the conception document reference_ **_NOT ISOLATED_**
The source
This record comes from experimental reaction archive (ord-067f9706b99f4ac98e07f49d63946447). Open the source and check it against what is on this page.
experimental reaction archive record ord-067f9706b99f4ac98e07f49d63946447 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.
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