Buchwald–Hartwig amination, record ord-ad4a7da8a91e4c23abc6ab58d6712f3f
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 | 2,5-Dichloro-4-iodopyridine | C₅H₂Cl₂IN | |
| Reactant | 2-amino-4-fluoro-N-methylbenzamide | C₈H₉FN₂O | |
| 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-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide | C₁₃H₁₀Cl₂FN₃O | 10.99% |
Conditions
- Temperature
- 80 °C
Yield
- 11% of 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide.
Procedure
Copied from the source record, unedited
palladium acetate (31.2 mg, 0.14 mmol) was added to 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (121 mg, 0.21 mmol), Cesium carbonate (2266 mg, 6.95 mmol), 2-amino-4-fluoro-N-methylbenzamide (585 mg, 3.48 mmol) and 2,5-dichloro-4-iodopyridine (1000 mg, 3.65 mmol) in dioxane (40 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18hrs then cooled. Product and bis product suggested. Disappointing! The reaction mixture was evaporated to dryness and redissolved in EtOAc (150 mL), and washed sequentially with saturated NaHCO3 (2 x 100 mL), water (100 mL), and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered then evaporated. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions
The source
This record comes from experimental reaction archive (ord-ad4a7da8a91e4c23abc6ab58d6712f3f). Open the source and check it against what is on this page.
experimental reaction archive record ord-ad4a7da8a91e4c23abc6ab58d6712f3f 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.