2-Bromo-5-methylpyridine → HCID 178426494, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottomed flask was added cis tert-butyl 4-aminocyclohexylcarbamate (0.5020 g, 2.342 mmol, Matrix Scientific), 2-bromo-5-methylpyridine (0.484 g, 2.81 mmol, Acros Organics), copper (0.012 g, 0.187 mmol, Fisher Scientific), and cesium acetate (2.79 g, 14.52 mmol, Sigma-Aldrich Chemical Company, Inc.) in DMSO (2.93 ml) to stir at 100° C. for 17 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic extract was washed with ammonium hydroxide, water, saturated NaCl, dried over MgSO4, filtered 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 (50 g), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide the title compound (279.5 mg, 0.915 mmol, 39.1% yield). LCMS showed product peak at 1.56 min (m+1=306.0).

Provenance & Evidence