Buchwald–Hartwig amination: 2-Bromo-4-iodoanisole → 3-Bromo-4-methoxy-N-[(oxan-4-yl)methyl]aniline

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

80 °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.

2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.

Every value is as the source recorded it. A run with no yield was reported without one, and nothing here is averaged, modelled or filled in.

Copied from the source record, unedited

Palladium (II) acetate (0.075 g, 0.34 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.223 g, 0.36 mmol) were suspended in dioxane (5mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 2-bromo-4-iodo-1-methoxybenzene (1.4 g, 4.47 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (0.547 mL, 4.47 mmol) and sodium-t- butoxide (0.645 g, 6.71 mmol) were suspended in dioxane (5ML). The resulting mixture was evacuated, purged with nitrogen and warmed to 50°C. After ~30 mins, the catalyst mixture was transferred to the reaction vessel. The reaction was evacuated and purged with nitrogen and heated at 80°C overnight. Very little product and mainly SM so reaction abandoned.

This record comes from experimental reaction archive (ord-6117c2ee846f49c3a77484ecf172e880). Open the source and check it against what is on this page.

• experimental reaction archive record ord-6117c2ee846f49c3a77484ecf172e880 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.