Buchwald–Hartwig amination: 2-Bromo-6-nitrotoluene → 1-[4-(2-Methyl-3-nitrophenyl)piperazin-1-yl]ethanone

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

Temperature

100 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

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.

• 1-[4-(5-Bromo-3-pyridinyl)piperazin-1-yl]ethanone32%
• 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone30%

Copied from the source record, unedited

1-bromo-2-methyl-3-nitrobenzene (500 mg, 2.31 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (201 mg, 0.35 mmol) and cesium carbonate (1131 mg, 3.47 mmol) and diacetoxypalladium (52.0 mg, 0.23 mmol) were dissolved in toluene (10 mL) and sealed into a microwave tube degazed and purged with argon. The reaction was heated to 100 °C, over a period of 12 hours. The reaction mixture was cooled down to room temperature, filtered and the residue was evaporated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% methanol in dichloromethane. The solvent was evaporated to dryness to afford 1-(4-(2-methyl-3-nitrophenyl)piperazin-1-yl)ethanone (600 mg, 98 %) as a solid.

This record comes from experimental reaction archive (ord-57be3c43ca2f40d482cab5a1bd42b5d5). Open the source and check it against what is on this page.

• experimental reaction archive record ord-57be3c43ca2f40d482cab5a1bd42b5d5 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

  experimental record · quality medium · source

experimental reaction record.