Buchwald–Hartwig amination, record ord-b57d9ea5b2ca4d5c93ac4813f00278f3
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-5-fluoro-N-methoxybenzamide | C₈H₉FN₂O₂ | |
| 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)pyridin-4-yl]amino]-5-fluoro-N-methoxybenzamide | C₁₉H₁₈F₄N₆O₂ | 67.7% |
Conditions
- Temperature
- 90 °C
Yield
- 68% of 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-5-fluoro-N-methoxybenzamide.
Procedure
Copied from the source record, unedited
N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (7.3 g, 19.10 mmol), 2-amino-5-fluoro-N-methoxybenzamide (5.28 g, 28.66 mmol), diacetoxypalladium (0.214 g, 0.96 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.105 g, 1.91 mmol) and cesium carbonate (12.45 g, 38.21 mmol) were suspended in 1,4-dioxane (76 ml). The reaction was degased, purged with nitrogen and heated to 90°C (internal temperature) overnight _._ Reaction was concentrated to dryness. Residue was diluted with EtOAc (200 mL) and water (200 mL). Aqueous was extracted with EtOAc (100 mL) then with EtOAc/MeOH 9/1 (100 mL) => _aqueous still contained some expected product._ Aqueous was saturated with NaCl and extracted with EtOAc/MeOH 9/1 (100 mL). Combined organic layers were dried over
The source
This record comes from experimental reaction archive (ord-b57d9ea5b2ca4d5c93ac4813f00278f3). Open the source and check it against what is on this page.
experimental reaction archive record ord-b57d9ea5b2ca4d5c93ac4813f00278f3 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.