Buchwald–Hartwig amination: 2,4-Dichloropyridine → 4-chloro-N-(2-methylpropyl)pyridin-2-amine
0% yield, run at 80 °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 | Isobutylamine | C₄H₁₁N | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)- | C₃₂H₆₂FeP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 4-chloro-N-(2-methylpropyl)pyridin-2-amine | C₉H₁₃ClN₂ | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of 4-chloro-N-(2-methylpropyl)pyridin-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%
- 4-chloro-N-pyridin-3-ylpyridin-2-amine51%
- 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-Benzyl-4-chloropyridin-2-amine0%
Procedure
Copied from the source record, unedited
palladium(II) acetate (0.018 g, 0.08 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (0.066 g, 0.12 mmol), sodium tert-butoxide (0.194 g, 2.02 mmol), 2-methylpropan-1-amine (0.100 mL, 1.01 mmol) and 2,4-dichloropyridine (0.151 mL, 1.01 mmol) were suspended in DME (4 mL) and sealed into a microwave tube. The reaction was heated to 80 °C for 30 minutes in the microwave reactor and cooled to RT.
The source
This record comes from experimental reaction archive (ord-ad988bfa2c604ea4b0ba123e57d761fa). Open the source and check it against what is on this page.
experimental reaction archive record ord-ad988bfa2c604ea4b0ba123e57d761fa 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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