Buchwald–Hartwig amination: 2,5-Dichloro-4-iodopyridine → 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide
32% yield, run at 80 °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-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-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide | C₁₃H₁₁Cl₂N₃O | 32.06% |
Conditions
- Temperature
- 80 °C
Yield
- 32% of 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide.
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.
- 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N-methylbenzamide77%
- 2-[2-Chloro-5-(trifluoromethyl)pyridin-4-ylamino]-N-methylbenzamide73%
- 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide69%
- 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-dichloropyridin-4-ylamino)-5-fluoro-N-methylbenzamide13%
Procedure
Copied from the source record, unedited
Palladium(II) acetate (0.098 g, 0.44 mmol) was added to 2,5-dichloro-4-iodopyridine (3 g, 10.95 mmol), 2-amino-N-methylbenzamide (1.645 g, 10.95 mmol), Cesium carbonate (7.14 g, 21.91 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.380 g, 0.66 mmol) in dioxane (150 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The crude residue was triturated with DCM to give a solid which was collected by filtration and dried under vacuum to give 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (1.58 g, 49 %) as a tan solid, LCMS indicated 87% pure. This was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to
The source
This record comes from experimental reaction archive (ord-36d41d697d8f415b8c7cc3a381080785). Open the source and check it against what is on this page.
experimental reaction archive record ord-36d41d697d8f415b8c7cc3a381080785 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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