Buchwald–Hartwig amination, record ord-f766bf8ef3f8450eb6d323fd10519896
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-N-methoxybenzamide | C₈H₁₀N₂O₂ | |
| 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-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide | C₁₃H₁₁Cl₂N₃O₂ | 39.07% |
Conditions
- Temperature
- 100 °C
Yield
- 39% of 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide.
Procedure
Copied from the source record, unedited
2,5-dichloro-4-iodopyridine (75 g, 273.84 mmol), 2-amino-N-methoxybenzamide (47.8 g, 287.53 mmol), cesium carbonate (107 g, 328.60 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (11.88 g, 20.54 mmol) were suspended in 1,4-dioxane (913 ml). Nitrogen was bubbled through the mixture for 20 minutes then diacetoxypalladium (3.07 g, 13.69 mmol) was added. Reaction was heated to reflux overnight under nitrogen. Reaction was allowed to cool to ~50°C and filtered. Filtered cake was washed with hot EtOH (2x300 mL) _._ Filtrate was concentrated to dryness to afford crude as a black solid (57 g). Filtered cake was re-washed with CH2Cl2/MeOH 9/1 (3x300 mL). Filtrate was combined with previous crude and concentrated to dryness to afford crude as a black solid (93 g). Crude was sti
The source
This record comes from experimental reaction archive (ord-f766bf8ef3f8450eb6d323fd10519896). Open the source and check it against what is on this page.
experimental reaction archive record ord-f766bf8ef3f8450eb6d323fd10519896 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.