Oxygen → 4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

Participants

Reaction Steps

To a stirred solution of (1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine 2 (0.887 mg, 3.52 mmol) in THF (10 mL), DMSO (2.5 mL), followed by KOtBu (25 mL, 1.0 M in THF) was added dropwise, and then the reaction mixture was treated with O2 for 15 min at room temperature, quenched with saturated NH4Cl (20 mL), extracted with EtOAc (3×60 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over Na2SO4 and evaporated. Flash chromatography of the residue over silica gel, using 20% EtOAc in hexanes to 40% EtOAc in hexanes) gave product 3 as a yellow solid. Yield: 560 mg (98%).

Provenance & Evidence