Buchwald–Hartwig amination: 2-Bromo-4-chlorobenzonitrile → 4-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]benzonitrile
69% 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 | 2-Bromo-4-chlorobenzonitrile | C₇H₃BrClN | |
| Reactant | (3S)-(-)-3-(Dimethylamino)pyrrolidine | C₆H₁₄N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 4-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]benzonitrile | C₁₃H₁₆ClN₃ | 69.34% |
Conditions
- Temperature
- 100 °C
Yield
- 69% of 4-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]benzonitrile.
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.
Procedure
Copied from the source record, unedited
A mixture of 2-bromo-4-chlorobenzonitrile (500 mg, 2.31 mmol), (S)-N,N-dimethylpyrrolidin-3-amine (317 mg, 2.77 mmol), cesium carbonate (1505 mg, 4.62 mmol), tris(dibenzylideneacetone)dipalladium(0) (212 mg, 0.23 mmol) and BINAP (288 mg, 0.46 mmol) in toluene (15 mL) was stirred at 100 °C for overnight. Conc. in vacuo, the residue was purified with ISCO (100% ethyl acetate to 30% methanol in ethyl acetate) to yield a light yellow solid as (S)-4-chloro-2-(3-(dimethylamino)pyrrolidin-1-yl)benzonitrile (400 mg, 69.3 %).
The source
This record comes from experimental reaction archive (ord-58bee23c6bfd4e46abec561eea6c720a). Open the source and check it against what is on this page.
experimental reaction archive record ord-58bee23c6bfd4e46abec561eea6c720a 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
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