Buchwald–Hartwig amination: 3-Bromo-2-methylpyridine → Tert-butyl 4-(2-methylpyridin-3-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-(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%
• Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate38%

Copied from the source record, unedited

RuPhos (0.543 g, 1.16 mmol) and palladium (II) acetate (0.131 g, 0.58 mmol) were suspended in toluene (15 mL) at ambient temperature. The resulting mixture was degassed and purged several times and warmed to 50°C under nitrogen for 20 mins. In a separate vessel were mixed 3-bromo-2-methylpyridine (2 g, 11.63 mmol), tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate (2.67 g, 83 %), sodium tertbutoxide (1.676 g, 17.44 mmol) and toluene. The mixture was degassed and purged with nitrogen several times and warmed to 50°C. The catalyst solution was added to the reaction vessel and the resulting mixture degassed and purged wtih nitrogen. The reaction was heated at 100°C overnight. The reaction mixture was allowed to cool to ambient temperature and filtered through GF/F paper, washing

This record comes from experimental reaction archive (ord-4147e405915e4ea7b4607546c536b535). Open the source and check it against what is on this page.

• experimental reaction archive record ord-4147e405915e4ea7b4607546c536b535 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.