1,4-Dioxane → 1H-Imidazo[4,5-b]pyridine-2-carbaldehyde

Participants

Reaction Steps

A mixture of vinylimidazo[4,5-b]pyridine (1 eq.), osmium tetroxide (0.1 eq.), sodium periodate (3-4 eq.), 1,4-dioxane (30 ml/mmol), and water (25 ml/mmol) is stirred for 15-30 min at ambient temperature. The resulting slurry is diluted with even amounts of water and ethyl acetate. After filtration through Celite®, the organic phase is dried over sodium sulfate, concentrated in vacuo and purified via flash chromatography to yield the respective formylimidazo[4,5-b]pyridine.

Provenance & Evidence