Buchwald–Hartwig amination: 4-Bromo-2-chlorobenzonitrile → Tert-butyl 4-(3-chloro-4-cyanophenyl)piperazine-1-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

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.

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.

• Methyl 4-(4-Boc-1-piperazinyl)-2-chlorobenzoate91%
• Tert-butyl 4-(7-benzo[b]furanyl)piperazine-1-carboxylate84%
• Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate83%
• Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate82%
• Tert-butyl 4-(5-(benzyloxy)pyridin-2-YL)piperazine-1-carboxylate69%
• tert-Butyl 4-(2-(ethoxycarbonyl)benzofuran-4-yl)piperazine-1-carboxylate64%
• Tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate62%
• tert-butyl 4-(2-methyl-3-oxo-1H-isoindol-5-yl)piperazine-1-carboxylate57%
• Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate52%
• tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate46%
• Tert-butyl 4-[6-[(4-methylsulfonylphenyl)methoxy]-3-pyridinyl]piperazine-1-carboxylate43%
• Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate38%

Copied from the source record, unedited

In a 250 mL round-bottomed dried flask , diacetoxypalladium (0.036 g, 0.16 mmol) was treated with 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.195 g, 0.31 mmol) under nitrogen in toluene (35 mL). The reaction was heated to 80 °C and was stirred for 10 min. To the flask was then added tert-butyl piperazine-1-carboxylate (0.602 g, 3.23 mmol), cesium carbonate (0.527 g, 1.62 mmol), potassium carbonate (0.447 g, 3.23 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (0.085 g, 0.32 mmol). The reaction was then treated with 4-bromo-2-chlorobenzonitrile (0.7 g, 3.23 mmol) and was allowed to stir at 80°C for 5 h. The mixture was then filtered over celite and celite was washed with heptanes. The mixture was condensed under reduced pressure and the crude material was purified on preparative HPLC MS

This record comes from experimental reaction archive (ord-80eaa5d6e27d4cf78d75715b3843cadc). Open the source and check it against what is on this page.

• experimental reaction archive record ord-80eaa5d6e27d4cf78d75715b3843cadc 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.