Buchwald–Hartwig amination: (2-Chloropyridin-4-yl)methanol → [2-(4-fluoro-N-methylanilino)-4-pyridinyl]methanol

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

105 °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.

• 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine12%
• methyl 2-(4-fluoro-N-methylanilino)pyridine-4-carboxylate0%
• 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine0%

Copied from the source record, unedited

In a 50 mL round-bottomed flask (t=g) was (2-chloropyridin-4-yl)methanol (.1 g, 0.70 mmol), Pd2dba3 (0.032 g, 0.03 mmol), and biphenyl-2-yldicyclohexylphosphine (0.024 g, 0.07 mmol) in toluene (6 mL) to give a dark red solution. 4-fluoro-N-methylaniline (0.096 g, 0.77 mmol) and KOtBu (.323 g, 2.88 mmol) were added. Mixture was degassed by bubbling N2 for 20 minutes, then placed in oil bath at 105 °C. Reaction went for 3 hours, at which point LC/MS was taken. No product was observed.

This record comes from experimental reaction archive (ord-eb19acfe7f704eb2aa769ff5f1767708). Open the source and check it against what is on this page.

• experimental reaction archive record ord-eb19acfe7f704eb2aa769ff5f1767708 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.