Boron tribromide → 3-Cyanomethyl-5-fluoro-2-methyl-7-(2-hydroxyphenacyl)pyrrolo[2,3-b]pyridine

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A mixture of 3-cyanomethyl-5-fluoro-2-methyl-7-(2-methoxyphenacyl)pyrrolo[2,3-b]pyridine hydrobromide (25 mg, 0.06 mmol), methylene chloride (2 ml), and BBr3 in methylene chloride (1M; 0.4 ml) under argon was refluxed for 8 h. The red gum was digested in a methylene chloride aqueous sodium bicarbonate mixture. The organic phase was dried over anhydrous Na2SO4, filtered, and evaporated to give a yellow crystalline product. Yield 19 mg (98%).

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