Iodine → 2-Iodo-6-(trifluoromethyl)pyridin-3-amine

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Reaction Steps

1.56 g (6.17 mmol) of iodine are added portionwise to a mixture, stirred under argon at 20° C., of 1 g (6.17 mmol) of 3-amino-6-trifluoromethylpyridine and 1.25 g (6.17 mmol) of silver sulfate in 40 ml of ethanol. Stirring is continued for 18 hours. The resulting yellow suspension is filtered and rinsed with ethanol. The filtrate is concentrated under reduced pressure and the residue is taken up in 100 ml of dichloromethane. The organic phase is successively washed with 20 ml of aqueous 5% sodium hydroxide solution, 40 ml of water and 20 ml of saturated aqueous sodium chloride solution, dried over sodium sulfate, concentrated under reduced pressure and then purified by chromatography on a column of silica (eluents: heptane/ethyl acetate). 1.17 g of the expected product are thus isolated, and are used without further purification in the following synthesis.

Provenance & Evidence