Buchwald–Hartwig amination: 2,4-Dichloropyridine → 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine
50% yield, run at 105 °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 | 2,4-Dichloropyridine | C₅H₃Cl₂N | |
| Reactant | 2-Methyl-2H-pyrazol-3-ylamine | C₄H₇N₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine | C₉H₉ClN₄ | 50.36% |
Conditions
- Temperature
- 105 °C
Yield
- 50% of 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine.
Procedure
Copied from the source record, unedited
TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (251 mg, 0.27 mmol) was [AP-added] to 2,4-dichloropyridine (1000mg, 6.76 mmol), 1-methyl-1H-pyrazol-5-amine (722 mg, 7.43 mmol), cesium carbonate (3302 mg, 10.14 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (461 mg, 0.80 mmol) in 1,4-dioxane (75 mL) warmed to 105ºC over a period of 21 hours under nitrogen. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL), and sequentially with water (25 mL). The organic layer was filtered using phase separating paper and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-chloro-N-(1-methyl-1H-pyrazol-5-yl)pyridin-2-amine (710
The source
This record comes from experimental reaction archive (ord-90d260fec9dd4d62a1593e5cdff9b43a). Open the source and check it against what is on this page.
experimental reaction archive record ord-90d260fec9dd4d62a1593e5cdff9b43a 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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