Buchwald–Hartwig amination: Methyl 4-bromobenzoate → Methyl 4-[(3,5-difluorophenyl)methylamino]benzoate

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.

Copied from the source record, unedited

methyl 4-bromobenzoate (1 g, 4.65 mmol), (3,5-difluorophenyl)methanamine (1.100 mL, 9.30 mmol) and Cesium carbonate (1.515 g, 4.65 mmol) were mixed in toluene (4 mL) and degassed by bubbling nitrogen through solution. Palladium acetate (0.052 g, 0.23 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.203 g, 0.33 mmol) were added and the vial was capped and heated at 100°C over 5 days. Workup by dilution with EtOAc, washing with water, then extraction with 2M HCl. The HCl extract was neutralized with 2M NaOH and extracted with EtOAc and the EtOAc phase was dried (K2CO3) and evaporated to give the crude product. The identity of product was doubtful but it was already used in exp 60-68.

This record comes from experimental reaction archive (ord-e2f4bb7b7a8a4f84a94e64c143c99234). Open the source and check it against what is on this page.

• experimental reaction archive record ord-e2f4bb7b7a8a4f84a94e64c143c99234 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.