Buchwald–Hartwig amination: 2-Bromo-isonicotinic acid methyl ester → methyl 2-(4-fluoro-N-methylanilino)pyridine-4-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

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%
• [2-(4-fluoro-N-methylanilino)-4-pyridinyl]methanol0%
• 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine0%

Copied from the source record, unedited

In a 100 mL round-bottomed flask (t=g) was methyl 2-bromoisonicotinate (.5 g, 2.31 mmol), 4-fluoro-N-methylaniline (0.348 g, 2.78 mmol), and CS2CO3 (1.056 g, 3.24 mmol) in toluene (16 mL) to give a yellow suspension. Pd2dba3 (0.106 g, 0.12 mmol) and biphenyl-2-yldicyclohexylphosphine (0.122 g, 0.35 mmol) were added. Reaction was allowed to stir overnight. LC/MS in the morning revealed little product had formed. Something with mass 272 dominated. Reaction was discarded.

This record comes from experimental reaction archive (ord-3a62166a30464afb9cbe502b267cbcba). Open the source and check it against what is on this page.

• experimental reaction archive record ord-3a62166a30464afb9cbe502b267cbcba 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.