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

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.

1. filtrationThe resulting yellow suspension is filtered
2. washrinsed with ethanol
3. concentrationThe filtrate is concentrated under reduced pressure
4. washThe 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
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. custompurified by chromatography on a column of silica (eluents: heptane/ethyl acetate)

ORD record

ord-8c41a1250efd4ad08f8ff45b8ca40ef4

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763636B2