Ethylene Glycol → HCID 86670438, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-pyridinethiol (633 mg, 3.33 mmol, Combi-Blocks, Inc., San Diego, Calif.), 2-chloro-5-iodopyridine (798 mg, 3.33 mmol, Sigma-Aldrich, St. Louis, Mo.), copper iodide (32 mg, 0.17 mmol, Strem Chemical Inc, Newburyport, Mass.), potassium carbonate (921 mg, 6.67 mmol), ethylene glycol (0.37 mL, 6.67 mmol), and 2-propanol (8 mL) were added to a reaction vial. The vial was sealed, purged with nitrogen for several minutes, and heated at 80° C. for 16 h. After cooling to room temperature, the solvents were removed under vacuum. The residue was absorbed onto a plug of silica gel and purified by chromatography through a silica gel column (40 g), eluting with a gradient of 0% to 10% EtOAc in hexanes, to provide 5-bromo-2-((6-chloro-3-pyridinyl)sulfanyl)pyridine (318 mg) as a white solid.

Provenance & Evidence