Buchwald–Hartwig amination: 6-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one → tert-butyl 4-(2-methyl-3-oxo-1H-isoindol-5-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

60 °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-(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

In an oven-dried RB flask was added Tris(dibenzylideneacetone)dipalladium(0) (0.046 g, 0.05 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.062 g, 0.10 mmol). The flask was evacuated and back-filled with nitrogen. Anhydrous toluene (3 mL) was added and the mixture was stirred at rt for 10 min to give a purple solution. 6-bromo-2-methylisoindolin-1-one (2.261 g, 10 mmol), 1-Boc-piperazine (1.863 g, 10.00 mmol) and Sodium tert-butoxide (1.714 mL, 14.00 mmol) were added in one portion followed by anhydrous toluene (15 mL). The flask was evacuated and back-filled with nitrogen and the resulting mixture was stirred at 60 °C under a nitrogen atmosphere for 2 days. LCMS shows 10% conversion. Tris(dibenzylideneacetone)dipalladium(0) (0.183 g, 0.20 mmol) and 2-Dicyclohexylphosphino-2',

This record comes from experimental reaction archive (ord-ce627b9c98e74957a0959e5bb6499f88). Open the source and check it against what is on this page.

• experimental reaction archive record ord-ce627b9c98e74957a0959e5bb6499f88 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.