2-Bromo-3-chloropyridine → 5-[(3-Chloro-2-pyridinyl)amino]-1-methylpiperidin-2-one

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In a 10 ml MW vial, Pd2((dba)3 (10.85 mg, 0.01 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (14.56 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (261 mg, 2.71 mmol), 5-amino-1-methylpiperidin-2-one (200 mg, 1.56 mmol) and 2-bromo-3-chloropyridine (300 mg, 1.56 mmol) mixed in toluene (3 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 for 1h then to rt for 2h. LC-MS 1h: 15% product. LC-MS o/n: 19% product. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 50g column. A gradient from 20% to 100% of EtOAc in heptane over 20CV was used as mobile phase. The product was collected using the wavelength 307 and 241 nm. Product was not found in any of the fractions, reaction discarded.

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