Buchwald–Hartwig amination, record ord-8d4927e597524dbea6e64f777b1f4296
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 3-Bromopyridine | C₅H₄BrN | |
| Reactant | 3-Aminopyridine | C₅H₆N₂ | |
| 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 | N-pyridin-3-ylpyridin-3-amine | C₁₀H₉N₃ | 3.62% |
Conditions
- Temperature
- 90 °C
Yield
- 4% of N-pyridin-3-ylpyridin-3-amine.
Procedure
Copied from the source record, unedited
Stock solution: 2.43 M solution of CyPF-tBu/Pd(OAc)2 (1:1) in DME. 3-bromopyridine (0.482 mL, 5.00 mmol) was dissolved in DME (10 mL). To the solution was added 2mL of stock solution, and sodium tert-butoxide (0.673 g, 7.00 mmol). To the mixture was added a solution of pyridin-3-amine (0.565 g, 6.00 mmol) in DME (10 mL). The mixture was heated at 90 °C overnight. LCMS showed the product formation, but the starting material 3-BrPy was still . To the mixture was added 2 mL stock solution additionally, and the mixture was heated at 90 °C for another 2h, but LCMS did not show improvement. The mixture was filtered. The filtrate was concentrated, and the compound was purified by preparative HPLC on a XBridge C18 column (10 µm 250x50 ID mm) using a gradient of 0-50% acetonitrile in H2O/ACN/NH3 9
The source
This record comes from experimental reaction archive (ord-8d4927e597524dbea6e64f777b1f4296). Open the source and check it against what is on this page.
experimental reaction archive record ord-8d4927e597524dbea6e64f777b1f4296 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.