Iodine → 4-Chloro-2-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

4-Chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (235 mg, 0.831 mmol) was dissolved in tetrahydrofuran (3 mL) under nitrogen atmosphere. After cooling to −78° C., n-butyllithium (0.675 mL, 1.080 mmol, 1.6 M hexane solution) was slowly added dropwise. The resulting mixture was stirred for 1 hour. After adding a solution of iodine (253 mg, 0.997 mmol) in tetrahydrofuran (2 mL), the mixture was slowly heated to room temperature. One hour later, the mixture was extracted with dichloromethane and water and the organic layer was washed with sodium chloride aqueous solution. The organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1) to give the target compound as a yellow oil (339 mg, 0.83 mmol, 97% yield).

Provenance & Evidence