Buchwald–Hartwig amination: 2,4-Dichloropyridine → 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine
10% yield, run at 200 °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 | 9.93% |
Conditions
- Temperature
- 200 °C
Yield
- 10% of 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine.
Procedure
Copied from the source record, unedited
2,4-dichloropyridine (100mg, 0.68 mmol), 1-methyl-1H-pyrazol-5-amine (72.2 mg, 0.74 mmol) and cesium carbonate (330 mg, 1.01 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (46.1 mg, 0.08 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (25.06 mg, 0.03 mmol) were suspended in 1,4-dioxane (5 mL) and sealed into a microwave tube. The reaction was heated to 200°C for 1 hour in the microwave reactor and cooled to RT. The reaction mixture was evaporated to dryness and redissolved in DCM (20 mL), and washed with water (20 mL). The organic layer was filtered with 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
The source
This record comes from experimental reaction archive (ord-1216a944f8b54fd3a989e124edb2145c). Open the source and check it against what is on this page.
experimental reaction archive record ord-1216a944f8b54fd3a989e124edb2145c 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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