Buchwald–Hartwig amination: 7-Bromoindole → tert-butyl 4-(1H-indol-7-yl)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

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.

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-(3-chloro-4-cyanophenyl)piperazine-1-carboxylate47%
• tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate46%
• Tert-butyl 4-[6-[(4-methylsulfonylphenyl)methoxy]-3-pyridinyl]piperazine-1-carboxylate43%

Copied from the source record, unedited

2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (75 mg, 0.16 mmol) and palladium (II) acetate (18.08 mg, 0.08 mmol) were dissoved in toluene (2 mL) at ambient temperature. The mixture was degassed and purged with nitrogen and warmed to 50°C for 20 mins. In a separate vessel, were mixed tert-butyl piperazine-1-carboxylate (300 mg, 1.61 mmol), 7-bromo-1H-indole (316 mg, 1.61 mmol) and sodium-t-butoxide (296 mL, 2.42 mmol) in toluene (3 mL). The mixture was degasssed and purged with nitrogen and warmed to 50°C. The catalyst solution was added to the reaction vessel and the resulting mixture was degassed and purged with nitrogen and heated at 100°C for overnight. UPLC analysis showed virtually no reaction (only 7% conversion to product). Reaction abandoned.

This record comes from experimental reaction archive (ord-b6527d32ba054a8395bc5ea7808e53a8). Open the source and check it against what is on this page.

• experimental reaction archive record ord-b6527d32ba054a8395bc5ea7808e53a8 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.