Buchwald–Hartwig amination: 5-Bromo-2-(4-methanesulfonylbenzyloxy)pyridine → Tert-butyl 4-[6-[(4-methylsulfonylphenyl)methoxy]-3-pyridinyl]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

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.

• 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-(pyridin-3-YL)piperazine-1-carboxylate38%

Copied from the source record, unedited

2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (48.3 mg, 0.08 mmol) was added in one portion to 5-bromo-2-(4-(methylsulfonyl)benzyloxy)pyridine (257.9 mg, 0.75 mmol), tert-butyl piperazine-1-carboxylate (160.9 mg, 0.86 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (51.1 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (120.1 mg, 1.25 mmol) in toluene (10 mL). N2 was bubbled through the solvent for 15 minutes.The resulting mixture was stirred at 80 °C for over night under N2.The reaction mixture was filtered through celite. The reaction mixture was evaporated to dryness and redissolved in EtOAc (75 mL), and washed sequentially with water (2x75 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purif

This record comes from experimental reaction archive (ord-b165e514f9f846c2872fe8f816e6b2d7). Open the source and check it against what is on this page.

• experimental reaction archive record ord-b165e514f9f846c2872fe8f816e6b2d7 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.