Buchwald–Hartwig amination: 2,6-Dichloropyridine → 6-chloro-N-phenylpyridin-2-amine
53% yield, run at 160 °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 | 2,6-Dichloropyridine | C₅H₃Cl₂N | |
| Reactant | Aniline | C₆H₇N | |
| Reagent | Potassium Carbonate | CK₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 6-chloro-N-phenylpyridin-2-amine | C₁₁H₉ClN₂ | 52.97% |
Conditions
- Temperature
- 160 °C
Yield
- 53% of 6-chloro-N-phenylpyridin-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.
- 4-Chloro-2-[(6-chloro-2-pyridinyl)amino]benzonitrile93%
- 2-Nitrodiphenylamine85%
- Methyl 3-anilino-5-bromobenzoate41%
- Methyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate2%
- Phenyl-pyridin-3-yl-aminenot recorded
- Methyl 3-anilino-5-bromobenzoate0%
- Phenyl-pyridin-3-yl-aminenot recorded
- Phenyl-pyridin-3-yl-aminenot recorded
- Phenyl-pyridin-3-yl-aminenot recorded
- Phenyl-pyridin-3-yl-aminenot recorded
- Phenyl-pyridin-3-yl-aminenot recorded
- Phenyl-pyridin-3-yl-aminenot recorded
Procedure
Copied from the source record, unedited
2,6-dichloropyridine (228 mg, 1.54 mmol) was dissolved in toluene (7.5 ml) and diacetoxypalladium (6 mg, 0.03 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (19 mg, 0.03 mmol), aniline (0.170 ml, 1.87 mmol) and potassium carbonate (583 mg, 4.22 mmol) were added added. The reaction mixture was sparged with notrogen for 3-4 minutes before being sealed into a microwave tube and heated to 160 °C over ~3 minutes, before holding at that temperature for 30 minutes. After cooling to ambient temperature the reaction mixture was diluted to ~40 mL with ethyl acetate and insoluble material removed by filtration. The filtrate was evaporated and purification attempted by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane. Product containing fractions were evaporated to drynes
The source
This record comes from experimental reaction archive (ord-a304a5abe5a040c6b1e32d87d537c8dc). Open the source and check it against what is on this page.
experimental reaction archive record ord-a304a5abe5a040c6b1e32d87d537c8dc 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
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.