Water → HCID 58910475, compound

Participants

Reaction Steps

87 mg (corresponding to 0.462 mmol) of 5-acetyl-2-(1H-imidazole-1-yl)pyridine was dissolved in 3.0 mL of dichloromethane and 193 μL of triethylamine, and then 120 μL (corresponding to 0.924 mmol) of bromotrimethylsilane was dropped under ice cooling. The resulting solution was stirred over night at room temperature under argon gas atmosphere, and then the reaction solution was supplemented with water and extracted 3 times with dichloromethane. The combined dichloromethane layer was washed with water and a saturated saline solution, and dried over magnesium sulfate. The solvent was distilled off, the resulting residue was dissolved in 3.0 mL of tetrahydrofuran, and 82.2 mg (corresponding to 0.462 mmol) of N-bromosuccinimide was added thereto under ice cooling. The resulting solution was stirred at room temperature for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by flash silica gel column chromatography (elution solvent: dichloromethane/ethyl acetate=2/1), to obtain 24.3 mg (corresponding to 0.091 mmol) of 5-(2-bromoacetyl)-2-(1H-imidazole-1-yl)pyridine (FIG. 3, step 2).

Provenance & Evidence