Buchwald–Hartwig amination: 4-Bromo-2-nitroanisole → 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone
1% yield, run at 120 °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 | 4-Bromo-2-nitroanisole | C₇H₆BrNO₃ | |
| Reactant | 1-Acetylpiperazine | C₆H₁₂N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone | C₁₃H₁₇N₃O₄ | 1.22% |
Conditions
- Temperature
- 120 °C
Yield
- 1% of 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone.
Procedure
Copied from the source record, unedited
4-bromo-1-methoxy-2-nitrobenzene (1.5 g, 6.46 mmol), 1-(piperazin-1-yl)ethanone (0.829 g, 6.46 mmol), CESIUM CARBONATE (4.21 g, 12.93 mmol), XANTPHOS (0.449 g, 0.78 mmol) and PdOAc2 (0.116 g, 0.52 mmol) were suspended in dioxane (20 ml) and sealed into a microwave tube. The reaction was heated to 120 °C for 90 minutes in the microwave reactor and cooled to RT. The reaction mixture was filtered through celite with ethyl acetate (50 mL). The filtrate was evaporated to dryness. The crude product was purified by flash silica chromatography in EtOAc. Pure fractions were evaporated to dryness to afford 1-(4-(4-methoxy-3-nitrophenyl)piperazin-1-yl)ethanone (0.022 g, 1.218 %) as a brown solid.
The source
This record comes from experimental reaction archive (ord-56a1dc90e93f4e37a4c4dceba5d45c4e). Open the source and check it against what is on this page.
experimental reaction archive record ord-56a1dc90e93f4e37a4c4dceba5d45c4e 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.
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