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

Silver sulfate (3.40 g, 10.9 mmol) and 2-amino-5-chloropyridine (1 g, 7.8 mmol) was added to a solution of iodine (2.76 g, 10.9 mmol) in ethanol (50 ml) and the reaction mixture stirred at rt for 72 h. The mixture was filtered, washed with methanol and the filtrate concentrated in vacuo. The residue was partitioned between saturated Na2S2O3 solution (50 ml) and DCM (2×50 ml). The combined organics were dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with DCM to give the title compound as a beige solid. δH (CDCl3): 4.95 (2H, br s), 7.84 (1H, d), 7.98 (1H, d).

1. filtrationThe mixture was filtered
2. washwashed with methanol
3. concentrationthe filtrate concentrated in vacuo
4. customThe residue was partitioned between saturated Na2S2O3 solution (50 ml) and DCM (2×50 ml)
5. dry with materialThe combined organics were dried (MgSO4)
6. concentrationconcentrated in vacuo
7. custompurified by chromatography on silica gel eluting with DCM

ORD record

ord-fead201bf4514fe38d8aba101316ffde

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158622B2