Ethanol → 2-Amino-5-fluoro-3-iodopyridine

5 g (44.6 mmol) of 2-amino-5-fluoropyridine, 13.9 g (44.6 mmol) of silver sulfate and 400 ml of ethanol are placed in a 500 ml two-necked flask equipped with a magnetic stirrer. 11.31 g (44.6 mmol) of iodine powder are then added portionwise. Stirring is continued at room temperature for 24 hours. The resulting yellow suspension is filtered, the precipitate is rinsed with ethanol and the filtrate is concentrated under reduced pressure. The residue thus obtained is taken up in a mixture of ethyl acetate (200 ml) and sodium carbonate solution (200 ml). After separation, the organic phase is successively washed with aqueous 25% sodium thiosulfate solution, with saturated aqueous sodium chloride solution and then dried over sodium sulfate and concentrated under reduced pressure. The resulting solid is purified by chromatography on a column of silica, eluting with a mixture of n-heptane and ethyl acetate. 2.67 g (11.22 mmol) of the expected product are obtained.

1. customequipped with a magnetic stirrer
2. filtrationThe resulting yellow suspension is filtered
3. washthe precipitate is rinsed with ethanol
4. concentrationthe filtrate is concentrated under reduced pressure
5. customThe residue thus obtained
6. customAfter separation
7. washthe organic phase is successively washed with aqueous 25% sodium thiosulfate solution, with saturated aqueous sodium chloride solution
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe resulting solid is purified by chromatography on a column of silica
11. washeluting with a mixture of n-heptane and ethyl acetate

ORD record

ord-f5bc8a71511d49de80cff6fab8b7966e

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763636B2