Buchwald–Hartwig amination: 1,4-Dibromobenzene → Methyl 2-(4-(4-bromophenyl)piperazin-1-yl)acetate

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

85 °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-Bromophenyl)-3-methylazetidine85%
• Ethyl 1-(4-bromophenyl)piperidine-4-carboxylate59%
• Methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate32%

Copied from the source record, unedited

In a reaction vial, 1,4-dibromobenzene (0.373 g, 1.58 mmol), methyl 2-(piperazin-1-yl)acetate (0.100 g, 0.63 mmol), CS2CO3 (0.309 g, 0.95 mmol), and BINAP (0.024 g, 0.04 mmol) were taken up in 1,4-dioxane (1.5 ml). Argon was bubbled through the solution for 1 minute. Pd2(dba)3 (0.012 g, 0.01 mmol) was added, followed by additional purging with argon. The vial was capped and placed on the heater-shaker. The reaction was stirred (450 rpm) at 100 °C overnight. LC/MS at this point did not indicate any formation of the dp. Experiment not progressed.

This record comes from experimental reaction archive (ord-cf737b8f3d9340aca6130b04f75e7c21). Open the source and check it against what is on this page.

• experimental reaction archive record ord-cf737b8f3d9340aca6130b04f75e7c21 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.