Diisobutylaluminum hydride → Imidazo(1,2-a)pyridine-8-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl imidazo[1,2-a]pyridine-8-carboxylate (1.76 g, 10 mmol) in toluene was added DIBAL (1M/THF, 20 ml) at −78° C. dropwise. The mixture was stirred at −78° C. for 1 h, quenched with MeOH (2 mL) and saturated NH4Cl solution (50 mL) and warmed up to rt. The mixture was continued to stir at rt for 1 h and diluted with DCM (60 mL). The aqueous layer was extracted with DCM (60 mL) twice. The combined organic layer was dried over MgSO4 and concentrate. The residue was purified on silica gel with 10% MeOH/DCM to give imidazo[1,2-a]pyridine-8-carbaldehyde (0.8 g, 55%). LRMS (M+H+) m/z 147.1.

Provenance & Evidence