Water → N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

Participants

Reaction Conditions

Reaction Steps

4.0 g (23.1 mmol) of 6-bromo-2-aminopyridine from example 14.1 were dissolved in 25 ml of dichloromethane and admixed with 4.1 ml (2.92 g, 28.9 mmol) of triethylamine. After cooling to 0° C., a solution of 3.1 ml (3.06 g, 25.4 mmol) of pivaloyl chloride in 5.0 ml of dichloromethane was added dropwise over a period of 10 min. The reaction mixture was allowed to warm to room temperature overnight and, for workup, poured onto 100 ml of dist. H2O. The phases were separated, the aqueous phase was extracted twice with 100 ml each time of ethyl acetate and the combined organic phases were dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and filtered through a short silica gel column (3×10 cm). After the solvent had been removed under reduced pressure, 5.73 g (22.3 mmol, 96.5%) of 6-bromo-2-pivaloylaminopyridine were obtained as a white solid.

Provenance & Evidence