Buchwald–Hartwig amination, record ord-96575886127b4df4af262fbd2602568c
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 | 1,3-dimethyl-1H-pyrazol-4-amine dihydrochloride | C₅H₁₁Cl₂N₃ | |
| Reactant | 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide | C₁₃H₁₀Cl₂FN₃O | |
| 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-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-4-fluoro-N-methylbenzamide | C₁₈H₁₈ClFN₆O | 3.92% |
Conditions
- Temperature
- 100 °C
Yield
- 4% of 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-4-fluoro-N-methylbenzamide.
Procedure
Copied from the source record, unedited
2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide (165 mg, 0.53 mmol), 1,3-dimethyl-1H-pyrazol-4-amine dihydrochloride (193 mg, 1.05 mmol), cesium carbonate (376 mg, 1.16 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (48.6 mg, 0.08 mmol) and diacetoxypalladium (9.43 mg, 0.04 mmol) were suspended in dioxane (3 mL) and sealed into a tube. The reaction was degased, purged with nitrogen and heated to 100 °C for 16 hours => _reaction not complete._ (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine), diacetoxypalladium and cesium carbonate were added. The reaction was degased, purged with nitrogen and heated to 110 °C for 4 hours => _reaction still not complete, no progress ..._ Reaction was filtered, washed with CH2Cl2 and concentrated to dryness. The react
The source
This record comes from experimental reaction archive (ord-96575886127b4df4af262fbd2602568c). Open the source and check it against what is on this page.
experimental reaction archive record ord-96575886127b4df4af262fbd2602568c 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.