Sodium Iodide → Ethyl 5-chloro-6-iodo-3-pyridinecarboxylate

To a solution of ethyl 5,6-dichloro-3-pyridinecarboxylate (1.00 g, 4.54 mmol) in propionitrile (30 ml) stirred under nitrogen at room temperature was added sodium iodide (2.044 g, 13.63 mmol) and iodotrimethylsilane (0.784 ml, 4.54 mmol). After stirring for 30 min, solvent was evaporated to dryness. The obtained brown oil was dissolved in water and pH was adjusted to basic with 2N NaOH. The aqueous phase was extracted with DCM, dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash chromatography using Flashmaster II, a 10 g silica gel cartridge, and mixtures of DCM/MeOH as eluent afforded a mixture of final product and ethyl 5-chloro-3-pyridinecarboxylate. The mixture was repurification by flash chromatography using Flashmaster II, a 50 g Merck silica gel cartridge, and mixtures of DCM/MeOH as eluent afforded the expected product ethyl 5-chloro-6-iodo-3-pyridinecarboxylate as a white solid.

1. customsolvent was evaporated to dryness
2. dissolutionThe obtained brown oil was dissolved in water
3. extractionThe aqueous phase was extracted with DCM
4. dry with materialdried over anhydrous MgSO4
5. concentrationconcentrated under reduced pressure
6. customPurification by flash chromatography
7. customa 10 g silica gel cartridge, and mixtures of DCM/MeOH as eluent afforded

ORD record

ord-dbb2593184944ecbab383f1ce7f8949b

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097628B2