Buchwald–Hartwig amination: 2,4-Dichloropyridine → 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine
60% yield, run at 130 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared 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 | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| 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 | 60.25% |
Conditions
- Temperature
- 130 °C
Yield
- 60% of 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Bis(dibenzylideneacetone)palladium | sodium 2-methylpropan-2-olate | 1,4-Dioxane | 130 °C | — | 60% (this run) |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Bis(dibenzylideneacetone)palladium | Cesium carbonate | 1,4-Dioxane | 105 °C | — | 23% |
Procedure
Copied from the source record, unedited
TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (1.238 g, 1.35 mmol) was added in one portion to 2,4-dichloropyridine (10g, 67.57 mmol), 1-methyl-1H-pyrazol-5-amine (7.22 g, 74.33 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.346 g, 4.05 mmol) and sodium tert-butoxide (9.74 g, 101.36 mmol) in 1,4-dioxane (500 mL) warmed to 130ºC over a period of 10 minutes under nitrogen. The resulting mixture was stirred at 130 °C for 24 hours. The reaction mixture was evaporated to dryness and redissolved in DCM (300 mL), and washed with water (125 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 4% MeOH in DCM. Pure fractions were evaporated to dryness to aff
The source
This record comes from experimental reaction archive (ord-dfcce3a0a05b417eb954f008fad9e74c). Open the source and check it against what is on this page.
experimental reaction archive record ord-dfcce3a0a05b417eb954f008fad9e74c 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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Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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