Buchwald–Hartwig amination, record ord-1f028ee237f04c2e9096e33f82aadddf
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 | 1-Bromo-4-fluorobenzene | C₆H₄BrF | |
| Reactant | Piperazin-2-one | C₄H₈N₂O | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 4-(4-Fluorophenyl)piperazin-2-one | C₁₀H₁₁FN₂O | 0% |
Conditions
- Temperature
- 150 °C
Yield
- 0% of 4-(4-Fluorophenyl)piperazin-2-one.
Procedure
Copied from the source record, unedited
diacetoxypalladium (11.21 mg, 0.05 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (28.9 mg, 0.05 mmol) were dissolved in toluene (0.5 mL) under nitrogen. Stirred at 50C for 30min. sodium 2-methylpropan-2-olate (96 mg, 1.00 mmol) and piperazin-2-one (50 mg, 0.50 mmol) were added to a second microwave vial and inerted with nitrogen. 1-bromo-4-fluorobenzene (0.110 mL, 1.00 mmol) and toluene (0.500 mL) were added. The catalyst solution wad added to the reaction mixture and the resulting solution was stirred at 100C for 1h in the microwave. No reaction. Heated to 150C for 1h, still no reaction, the reaction was discarded.
The source
This record comes from experimental reaction archive (ord-1f028ee237f04c2e9096e33f82aadddf). Open the source and check it against what is on this page.
experimental reaction archive record ord-1f028ee237f04c2e9096e33f82aadddf 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.