Buchwald–Hartwig amination, record ord-3b22658007fa466891096d7c97ab437d
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 | 2-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-yl)pyridin-2-amine | C₁₀H₉N₃ | 22.2% |
Conditions
- Temperature
- 90 °C
Yield
- 22% of N-(Pyridin-3-yl)pyridin-2-amine.
Procedure
Copied from the source record, unedited
Stock solution: 0.01 mmol Pd and ligand were dissolved in 2 mL DME. 3-bromopyridine (0.482 mL, 5.00 mmol) was dissolved in DME (10 mL). To the solution was added the stock solution, and sodium tert-butoxide (0.673 g, 7.00 mmol). To the mixture was added a solution of pyridin-2-amine (0.565 g, 6.00 mmol) in DME (10 mL). The mixture was heated at 90 °C overnight. 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 95/5/0.2 buffer over 15 minutes with a flow of 100 mL/min. The compounds were detected by UV at 254nm. To the fractions (ca. 60mL) were added 5 mL of HOAc. The product was freezing-dried to give the product N-(pyridin-3-yl)pyridi
The source
This record comes from experimental reaction archive (ord-3b22658007fa466891096d7c97ab437d). Open the source and check it against what is on this page.
experimental reaction archive record ord-3b22658007fa466891096d7c97ab437d 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.