Buchwald–Hartwig amination: 3-(2-Chloropyridin-4-yl)oxy-2,6-dimethyl-pyridine → 4-(2,6-Dimethylpyridin-3-yloxy)-N-(4-(methylsulfonyl)phenyl)pyridin-2-amine
51% yield, run at 150 °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 | 3-(2-Chloropyridin-4-yl)oxy-2,6-dimethyl-pyridine | C₁₂H₁₁ClN₂O | |
| Reactant | 4-(Methylsulfonyl)aniline | C₇H₉NO₂S | |
| 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 | Dimethylacetamide | C₄H₉NO | |
| Product | 4-(2,6-Dimethylpyridin-3-yloxy)-N-(4-(methylsulfonyl)phenyl)pyridin-2-amine | C₁₉H₁₉N₃O₃S | 50.82% |
Conditions
- Temperature
- 150 °C
Yield
- 51% of 4-(2,6-Dimethylpyridin-3-yloxy)-N-(4-(methylsulfonyl)phenyl)pyridin-2-amine.
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.
Procedure
Copied from the source record, unedited
In a 10 mL microwave reactor 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (100 mg, 0.43 mmol) and 4-(methylsulfonyl)aniline (73.0 mg, 0.43 mmol) were dissolved in DMA (3 mL) to give a tan solution.To the resultant solution Cesium carbonate (0.068 mL, 0.85 mmol) was added and sparged with nitrogen for 1 minute. Then Palladium(II) acetate (6.70 mg, 0.03 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (29.6 mg, 0.05 mmol) were added and the reaction mixture was sealed. The reaction was heated to150 °C for 25 minutes in the biotage microwave.The reaction was cooled to room temperature and LCMS shows reaction was completed. Reaction mixture was filtered through Celite Bed and washed with Dichloromethane. Filtrate was subjected to concentration to get DMA solution which was given t
The source
This record comes from experimental reaction archive (ord-0a36562a530a4f6bb99c0bf4c44fc018). Open the source and check it against what is on this page.
experimental reaction archive record ord-0a36562a530a4f6bb99c0bf4c44fc018 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
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