Buchwald–Hartwig amination, record ord-10a49d7456a04dcab0790ed1d012aba2
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-6-methoxy-N-methylbenzamide | C₉H₁₂N₂O₂ | |
| 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]-6-methoxy-N-methyl-benzamide | C₂₀H₂₁F₃N₆O₂ | 58.53% |
Conditions
- Temperature
- 100 °C
Yield
- 59% of 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-6-methoxy-N-methyl-benzamide.
Procedure
Copied from the source record, unedited
To a stirred solution of N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (26 g, 68.04 mmol) and 2-amino-6-methoxy-N-methylbenzamide (18.39 g, 102.06 mmol) in dioxane (300 mL) is added cesium carbonate (39.9 g, 122.47 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (3.94 g, 6.80 mmol) and diacetoxypalladium (0.764 g, 3.40 mmol). Mixture was degassed 3 times with N2 and heated to 100°C overnight. LCMS crude seems OK. Reaction was cooled to room temperature then salts were filtered and the filtrate concentrated to afford a crude compound which was purified on silica, eluting with 5% MeOH in AcOEt. Solvent were evaporated to afford a gum which finished by crystallize in 100mL of CH2Cl2. Solid was filtered and dried to a constant weight to afford
The source
This record comes from experimental reaction archive (ord-10a49d7456a04dcab0790ed1d012aba2). Open the source and check it against what is on this page.
experimental reaction archive record ord-10a49d7456a04dcab0790ed1d012aba2 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.