Buchwald–Hartwig amination, record ord-d638b772d95f46ee990c617a7a9864d8
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 | 2-Chloro-4-iodo-5-(trifluoromethyl)pyridine | C₆H₂ClF₃IN | |
| Reactant | 2-Amino-N-methylbenzamide | C₈H₁₀N₂O | |
| 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-Chloro-5-(trifluoromethyl)pyridin-4-ylamino]-N-methylbenzamide | C₁₄H₁₁ClF₃N₃O | 67.4% |
Conditions
- Temperature
- 90 °C
Yield
- 67% of 2-[2-Chloro-5-(trifluoromethyl)pyridin-4-ylamino]-N-methylbenzamide.
Procedure
Copied from the source record, unedited
2-chloro-4-iodo-5-(trifluoromethyl)pyridine (7 g, 22.77 mmol), 2-amino-N- methylbenzamide (3.42 g, 22.77 mmol), diacetoxypalladium (0.409 g, 1.82 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.108 g, 3.64 mmol) and cesium carbonate (8.90 g, 27.32 mmol) were mixed together in dioxane (140 mL). Reaction was degassed with nitrogen and was stirred at 90 °C overnight under nitrogen. Reaction was filtered, washed with CH2Cl2 and filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10 to 50% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (5.06 g, 67.4 %) as a pale yellow solid.
The source
This record comes from experimental reaction archive (ord-d638b772d95f46ee990c617a7a9864d8). Open the source and check it against what is on this page.
experimental reaction archive record ord-d638b772d95f46ee990c617a7a9864d8 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.