Iodine → 2-Amino-5-chloro-3-iodopyridine

Iodine (7.55 g; 29.73 mmol) was added to a mixture of 5-chloropyridin-2-amine (3.00 g; 22.87 mmol) and silver sulfate (9.36 g; 29.73 mmol) in ethanol (150 mL) and the mixture was stirred overnight at room temperature. The mixture was filtered over celite, washed with ethanol, and the filtrate concentrated in vacuo. The residue was dissolved in dichloromethane, and the solution was washed with a saturated aqueous solution of sodium thiosulfate. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and the residue purified by flash chromatography on silica gel (eluent 0 to 30% ethyl acetate in heptane) to give 3.71 g (64%) of 5-chloro-3-iodopyridin-2-amine as a beige solid.

1. filtrationThe mixture was filtered over celite
2. washwashed with ethanol
3. concentrationthe filtrate concentrated in vacuo
4. dissolutionThe residue was dissolved in dichloromethane
5. washthe solution was washed with a saturated aqueous solution of sodium thiosulfate
6. dry with materialThe organic layer was dried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customthe residue purified by flash chromatography on silica gel (eluent 0 to 30% ethyl acetate in heptane)

ORD record

ord-3ea2dad19cf7484589b94fb9e60c71d6

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266832B2