Buchwald–Hartwig amination: 2,5-Dichloro-4-iodopyridine → 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide
69% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
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 | 69.18% |
Conditions
- Temperature
- 100 °C
Yield
- 69% of 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- N-methoxy-2-[[5-(trifluoromethyl)-2-[(1,3,5-trimethylpyrazol-4-yl)amino]pyridin-4-yl]amino]benzamide89%
- 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-N-methoxy-benzamide49%
- 8-[(2,5-Dichloropyridin-4-yl)amino]-2-methyl-3,4-dihydroisoquinolin-1-one43%
- 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide35%
- 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide32%
- 2-(2,5-dichloropyridin-4-ylamino)-5-fluoro-N-methylbenzamide13%
Procedure
Copied from the source record, unedited
2,5-dichloro-4-iodopyridine (10.4 g, 37.97 mmol), 2-amino-N-methoxybenzamide (6.63 g, 39.87 mmol), cesium carbonate (14.85 g, 45.57 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.648 g, 2.85 mmol) were suspended in 1,4-dioxane (130 mL). Nitrogen was bubbled through the mixture for 10 minutes then diacetoxypalladium (0.426 g, 1.90 mmol) was added. Flask was purged with nitrogen 3 times and heated to reflux for 16 hours. Reaction was allowed to cool to room temperature and diluted with CH2Cl2 (100 mL) (=> _trouble_ ) + MeOH (10 mL). Mixture was filtered _(filtrate is clear)_ and washed with CH2Cl2/MeOH 9/1 (2x100 mL) => _filtrate became troubled._ Filtrate was concentrated to dryness to afford crude as a dark brown solid (17.5 g). Filtered cake seemed to contain some
The source
This record comes from experimental reaction archive (ord-aaefdd638c464adeb91c856ec0ce39ed). Open the source and check it against what is on this page.
experimental reaction archive record ord-aaefdd638c464adeb91c856ec0ce39ed 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.
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