Buchwald–Hartwig amination: 2-Bromo-5-fluorobenzaldehyde → 5-Fluoro-2-(pyrrolidin-1-yl)benzaldehyde
0% yield, run at 95 °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-5-fluorobenzaldehyde | C₇H₄BrFO | |
| Reactant | Pyrrolidine | C₄H₉N | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-Fluoro-2-(pyrrolidin-1-yl)benzaldehyde | C₁₁H₁₂FNO | 0% |
Conditions
- Temperature
- 95 °C
Yield
- 0% of 5-Fluoro-2-(pyrrolidin-1-yl)benzaldehyde.
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
To a mixture of pyrrolidine (328 mg, 3.05 mmol), 2-bromo-4-fluorobenzaldehyde (619 mg, 3.05 mmol) in toluene (10 ml) was added Cs2CO3 (2.48g, 7.62 mmol), BINAP (95 mg ) and palladium(II) acetate (35 mg) was added. The mixture was purged with Ar for 5 min, then heated at 95 oC for 4 hrs. After cooled to RT, EtOAc (30 mL) was added. The organic layer was washed with water (3 x 30 mL), brine (30 mL), dried over MgSO4, filetred and concentrated. The residue was purified via combiflush (0 - 20% EtOAc/Hexane; 40 g column) to give the desired product as a clear reddish liquid. LCMS and H-NMR look good. 290 mg Conclusion: reaction progressed to give desired product in 49% yield.
The source
This record comes from experimental reaction archive (ord-ac71d193208d45949ee247d7a0855249). Open the source and check it against what is on this page.
experimental reaction archive record ord-ac71d193208d45949ee247d7a0855249 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.
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