2-Bromo-5-methylpyridine → HCID 178426495, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl trans-4-aminocyclohexylcarbamate (1.9965 g, 9.32 mmol), 2-bromo -5-methylpyridine (1.923 g, 11.18 mmol), copper (0.047 g, 0.745 mmol), and cesium acetate (11.09 g, 57.8 mmol) were suspended in dry DMSO (11.65 ml) and stirred at 100° C. for 22 hours. The reaction was allowed to cool to room temperature. The reaction mixture was diluted with 1N sodium hydroxide and extracted with ethyl acetate. The organic extract was washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (100 g), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide tert-butyl(trans-4-((5-methylpyridin-2-yl)amino)cyclohexyl)carbamate (0.9695 g, 3.17 mmol, 34.1% yield).

Provenance & Evidence