Buchwald–Hartwig amination: 2-Bromo-N,N-dimethylaniline → Tert-butyl 4-[2-(dimethylamino)phenyl]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

Palladium (II) acetate (67.3 mg, 0.30 mmol) and 2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (280 mg, 0.60 mmol) were dissolved in toluene (7 mL) and purged with nitrogen. The mixture was warmed to 50°C for 15 mins. In a separate vessel, were mixed 2-bromo-N,N-dimethylaniline (600 mg, 3.00 mmol), tert-butyl piperazine-1-carboxylate (559 mg, 3.00 mmol) and sodium-t- butoxide (432 mg, 4.50 mmol) in toluene (8 mL). The mixture was degassed and purged with nitrogen. The catalyst solution was added and the resulting mixture heated at 100°C overnight. The reaction mixture was filtered through celite, washing with MeOH/EtOAc. The filtrate was concentrated and purified by flash silica chromatography, elution gradient 0 to 70% EtOAc in heptane. Pure fractions were evaporated to drynes

This record comes from experimental reaction archive (ord-3ee1bec4d5b244e8a0d82f023c1c6526). Open the source and check it against what is on this page.

• experimental reaction archive record ord-3ee1bec4d5b244e8a0d82f023c1c6526 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.