1,4-Dioxane → 5-Bromo-3-ethylpyridin-2-amine

Participants

Reaction Steps

To a solution prepared by dissolving 360 mg of 3-ethylpyridine-2-amine (synthesized according to the method disclosed in International Publication WO2006/025567, page 142) in a mixed solvent of 12 mL of 1,4-dioxane and 4 mL of water, 553 mg of N-bromosuccinimide was added at 0° C., and the mixture was stirred for 1.5 hours at the same temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer thus obtained was washed with water and saturated brine in that order, and dried over anhydrous sodium sulfate. Thereafter, the insolubles were filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=75/25), to obtain 394 mg of 5-bromo-3-ethylpyridine-2-amine [33-1] (hereinafter, referred to as the compound [33-1]).

Provenance & Evidence