Buchwald–Hartwig amination: Iodobenzene → methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate

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

9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (441 mg, 0.76 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (279 mg, 0.30 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (16.600 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and then heated to 50ºC for 10 minutes. Cesium carbonate (6204 mg, 19.04 mmol), methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate (1700 mg, 7.62 mmol) and Iodobenzene (1.023 ml, 9.14 mmol) were stirred in anisole (33.2 ml), the flask was evacuated and flushed with nitrogen three times and then heated to 50ºC. The catalyst mixture was transferred into the flask with the reactants (by syringe) and the mixture heated to 100 °C for 18 hours. The reaction mixture was di

This record comes from experimental reaction archive (ord-1169cbe9fa064a879ac34b2e524a4e69). Open the source and check it against what is on this page.

• experimental reaction archive record ord-1169cbe9fa064a879ac34b2e524a4e69 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

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experimental reaction record.