Iodine → 6-Chloro-2-iodopyridin-3-amine

Temperature

20 °C

To a solution of 6-chloro-pyridin-3-ylamine (10.0 g, 77.8 mmol) in EtOH (150 mL) was added Ag2SO4 (12.1 g, 38.9 mmol) and I2 (23.7 g, 93.4 mmol) at room temperature. The mixture was stirred at 20° C. overnight. The solvent was removed by evaporation under vacuum. Water (100 mL) and EtOAc (200 mL) were added to the residue. The organic layer was separated and the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate 7:1) to give 6-chloro-2-iodo-pyridin-3-ylamine (17.1 g, 86%). 1H NMR (DMSO, 300 MHz) δ 7.16 (d, J=8.4 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 5.57 (s, 2H).

1. customThe solvent was removed by evaporation under vacuum
2. additionWater (100 mL) and EtOAc (200 mL) were added to the residue
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
6. customevaporated under vacuum
7. customto give the crude product, which
8. customwas purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate 7:1)

ORD record

ord-d2437703155c4cd1a5bc4237e838f9fc

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563573B2