Buchwald–Hartwig amination: 2,4-Dichloropyridine → 4-chloro-N-pyridin-3-ylpyridin-2-amine
51% yield, run at 100 °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 | 3-Aminopyridine | C₅H₆N₂ | |
| 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 | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-chloro-N-pyridin-3-ylpyridin-2-amine | C₁₀H₈ClN₃ | 51.48% |
Conditions
- Temperature
- 100 °C
Yield
- 51% of 4-chloro-N-pyridin-3-ylpyridin-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.
- N-(4-chloro-2-pyridinyl)-2,6-dimethylpyrimidin-4-amine61%
- 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine60%
- N-(4-chloro-2-pyridinyl)-4-methylpyrimidin-2-amine58%
- N-(4-chloro-2-pyridinyl)pyrimidin-2-amine55%
- N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine50%
- Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate48%
- Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-4-carboxylate37%
- N-(4-chloro-2-pyridinyl)-4-methyl-1,3-oxazol-2-amine28%
- N-(4-chloro-2-pyridinyl)-4-(trifluoromethyl)-1,3-oxazol-2-amine17%
- N-(4-chloro-2-pyridinyl)-4,5-dimethyl-1,3-oxazol-2-amine15%
- N-pyridin-3-ylpyridin-3-amine4%
- N-Benzyl-4-chloropyridin-2-amine0%
Procedure
Copied from the source record, unedited
pyridin-3-amine (95 mg, 1.01 mmol), 2,4-dichloropyridine (0.151 mL, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in dioxane (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.10 mmol) was added and the mixture heated at 100 °C for 2h. The mixture was cooled, filtered and concentrated. The crude product was purified by flash silica chromatography, eluting gradient 5-45% EtOAc in isohexane. Fractions were evaporated to dryness and purified by flash silica chromatography, eluting at 35% EtOAc in isohexane to afford 4-chloro-N-(pyridin-3-yl)pyridin-2-amine (107 mg, 51.5 %) as a cream powder.
The source
This record comes from experimental reaction archive (ord-3c36e457f5e64b5b9130db89ea6a541e). Open the source and check it against what is on this page.
experimental reaction archive record ord-3c36e457f5e64b5b9130db89ea6a541e 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.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.
Where to next
More Buchwald–Hartwig amination records
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