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0 °C

To a solution of 1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine (2) (0.887 g, 3.51 mmole) in anhydrous THF (10 mL) dimethyl sulfoxide (25 mL) was added slowly (via a syringe) and the mixture was cooled to 0° C. Potassium tert-butoxide (1M in THF, 25 mL, 25 mmole) was added slowly. Oxygen was bubbled through the mixture for 45 minutes. The reaction was quenched with saturated ammonium chloride solution, the mixture was extracted with ethyl acetate (3×50 mL). The organic layer was separated, dried over magnesium sulphate and concentrated. The residue was purified by column chromatography (3:1 Hex:EtOAc) to afford intermediate (3). Yield: 1.06 g >100%

1. customOxygen was bubbled through the mixture for 45 minutes
2. customThe reaction was quenched with saturated ammonium chloride solution
3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
4. customThe organic layer was separated
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated
7. customThe residue was purified by column chromatography (3:1 Hex:EtOAc)