Buchwald–Hartwig amination, record ord-f57bbfadfec74fbbad7d399cf7b15368
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 | 46.21% |
Conditions
- Temperature
- 95 °C
Yield
- 46% 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 (113 mg, 0.30 mmol), 2-amino-5-fluoro-N-methoxybenzamide (60 mg, 0.33 mmol) and Cesium carbonate (193 mg, 0.59 mmol) in degassed dioxane (4 mL) under nitrogen at room temperature were degassed (nitrogen) for a further 5 minutes before adding Palladium(II) acetate (3.32 mg, 0.01 mmol) and 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (17.14 mg, 0.03 mmol) the reaction mixture then being allowed to stir at 95 °C for 6 hours and cooled to RT. LCMS analysis showed a new peak for product (9%) but both SM's still remained (pyridine 71%, benzamide 13 %). Another 1.1 eq of benzamide (60 mg in 2ml dioxane) was added and the RM was then heated at 95 °C overnight. Lcms after this time showed no further progression with the r
The source
This record comes from experimental reaction archive (ord-f57bbfadfec74fbbad7d399cf7b15368). Open the source and check it against what is on this page.
experimental reaction archive record ord-f57bbfadfec74fbbad7d399cf7b15368 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.