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Example 12 Synthesis of 4-bromo-5-methoxyindole (XLVI): to a solution of 2-bromo-4-nitroanisole (1.16 g, 5 mmol) in tetrahydrofuran (THF, 10 ml) was slowly added vinylmagnesium bromide (1 M solution in THF, 15 ml) at -40 °C. The reaction mixture was stirred at this temperature for 30 min, followed by a slow warming to -20 °C. Upon completion of the reaction, the reaction was quenched by the addition of saturated ammonium chloride (NH4Cl) solution and subsequently diluted with ether (Et2O). The aqueous layer was extracted twice with ether (Et2O). All organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated. Purification by fast chromatography (eluent: hexane/ethyl acetate) gave 4-bromo-5-methoxyindole (XLVI, 38 mg, 3% yield) as an oil.