Buchwald–Hartwig amination: 2-Chloroquinoline → tert-Butyl 4-(quinolin-2-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-[6-[(4-methylsulfonylphenyl)methoxy]-3-pyridinyl]piperazine-1-carboxylate43%
• Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate38%

Copied from the source record, unedited

A 2.0-5.0 mL microwave vial was charged with tert-Butyl 1-piperazinecarboxylate (100 mg, 0.54 mmol), 2-Chloroquinoline (0.086 mL, 0.64 mmol), Sodium tert-butoxide (61.9 mg, 0.64 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (33.4 mg, 0.05 mmol) and toluene (3 mL). The reaction mixture was degassed for 10 minutes with nitrogen, and then Tris(dibenzylideneacetone)dipalladium(0) (24.58 mg, 0.03 mmol) was added. The reaction mixture was stirred at 100°C in an oil bath for 12h. The solution was diluted with EtOAc and washed with saturated NaHCO3, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was loaded on a 40g silica gel column and purified on a Teledyne Isco instrument, eluting with 10% to 40% ethyl acetate in heptane. Product

This record comes from experimental reaction archive (ord-70ea34f4ab314aa093c5c77488bf98e8). Open the source and check it against what is on this page.

• experimental reaction archive record ord-70ea34f4ab314aa093c5c77488bf98e8 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.