Buchwald–Hartwig amination: 3-(2-Chloropyridin-4-yl)oxy-2,6-dimethyl-pyridine → 4-[[4-[(2,6-Dimethyl-3-pyridinyl)oxy]-2-pyridinyl]amino]-N-(2-methoxy-1-methylethyl)benzenesulfonamide
52% 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-amino-N-(1-methoxypropan-2-yl)benzene-1-sulfonamide | C₁₀H₁₆N₂O₃S | |
| 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-[[4-[(2,6-Dimethyl-3-pyridinyl)oxy]-2-pyridinyl]amino]-N-(2-methoxy-1-methylethyl)benzenesulfonamide | C₂₂H₂₆N₄O₄S | 51.97% |
Conditions
- Temperature
- 150 °C
Yield
- 52% of 4-[[4-[(2,6-Dimethyl-3-pyridinyl)oxy]-2-pyridinyl]amino]-N-(2-methoxy-1-methylethyl)benzenesulfonamide.
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-amino-N-(1-methoxypropan-2-yl)benzenesulfonamide (104 mg, 0.43 mmol) were dissolved in DMA (3 mL) to give a brown 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
The source
This record comes from experimental reaction archive (ord-067637c197bb4672875d64a38b7940ee). Open the source and check it against what is on this page.
experimental reaction archive record ord-067637c197bb4672875d64a38b7940ee 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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