Buchwald–Hartwig amination: 3-Bromopyridine → N-pyridin-3-ylpyridin-3-amine
10% 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 | 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 | 9.97% |
Conditions
- Temperature
- 100 °C
Yield
- 10% 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. pyridin-3-amine (3.57 g, 37.98 mmol) was dissolved in DME (10 mL). To the mixture was added 10 mL of stock solution, and sodium tert-butoxide (4.26 g, 44.30 mmol). 5 min later, to the mixtue was added a solution of 3-bromopyridine (3.05 mL, 31.65 mmol) in DME (10 mL). The mixture was heated at 100 °C overnight. LCMS1 showed the result after 1 h heating. LCMS2 showed the result after 18 h heating, which showed the product formation, and the starting material 3-BrPy. LCMS3 showed the result after 40 h heating. LCMS4 was after 60h. To the mixture was added 50 mL DCM and acetic acid (2 mL, 34.94 mmol). The mixture was stirred for 10 min, and then was filtered. The filtrate was concentrated, and the compound was purified by pr
The source
This record comes from experimental reaction archive (ord-acf9860e722c4b4598d1b2c19d9e27a1). Open the source and check it against what is on this page.
experimental reaction archive record ord-acf9860e722c4b4598d1b2c19d9e27a1 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
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