Buchwald–Hartwig amination: Methyl 4-Bromo-2-chlorobenzoate → Methyl 4-(4-Boc-1-piperazinyl)-2-chlorobenzoate

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.

• 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%
• Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate38%

Copied from the source record, unedited

To a solution of palladium acetate (18.00 mg, 0.08 mmol) in dry toluene (16 mL) under nitrogen was added BINAP (100 mg, 0.16 mmol). The reaction was heated to 80 °C and stirred for 10 min. To the reaction was then added tert- butyl piperazine-1-carboxylate (299 mg, 1.60 mmol), cesium carbonate (261 mg, 0.80 mmol), potassium carbonate (222 mg, 1.60 mmol), 18-crown-6 (42.4 mg, 0.16 mmol) and methyl 4-bromo-2-chlorobenzoate (400 mg, 1.60 mmol). The reaction was stirred at 80°C overnight, filtered through celite and washed with small amounts of DCM. The filtrate was concentrated under reduced pressure and purified by flash chromatography on silica gel, eluting with mixtures of EtOAc and heptane, to afford tert-butyl 4-(3-chloro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate (517 mg, 91 %)

This record comes from experimental reaction archive (ord-879a784e2da64b7f993840feec5d14ac). Open the source and check it against what is on this page.

• experimental reaction archive record ord-879a784e2da64b7f993840feec5d14ac 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.