Buchwald–Hartwig amination: 2-Bromo-3-chloropyridine → (3R)-3-[(3-chloro-2-pyridinyl)amino]piperidin-2-one

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

115 °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.

• 3-chloro-N-cyclobutylpyridin-2-amine25%
• 3-chloro-N-[(3-methyloxetan-3-yl)methyl]pyridin-2-amine12%
• 5-[(3-Chloro-2-pyridinyl)amino]-1-methylpiperidin-2-one0%

Copied from the source record, unedited

In a 5 ml MW vial, Pd2((dba)3 (7.23 mg, 7.90 µmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (9.71 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (174 mg, 1.81 mmol), (R)-3-aminopiperidin-2-one (119 mg, 1.04 mmol) and 2-bromo-3-chloropyridine (200 mg, 1.04 mmol) mixed in toluene (2 mL) to give a brown suspension. The mixture was degassed with N2 bubbling for 5 min, then the vial was capped and the reaction stirred at 115°C in an oil-bath over night. The reaction was cooled to rt, DCM and aq NaHCO3 were added, the mixture stirred, filtered through a phase separator and evaporated. LC-MS crude: Traces of product, mainly starting bromide left. Reaction discarded.

This record comes from experimental reaction archive (ord-945adafe269741f9bc504b4e9b38a0a3). Open the source and check it against what is on this page.

• experimental reaction archive record ord-945adafe269741f9bc504b4e9b38a0a3 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.