Chloroform → 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

1.00 g (6.75 mmol) of 3-methyl-1H-pyrrolo[2,3-b]pyridine 7-oxide (from example XXXVII) is suspended in 5 ml of phosphoryl chloride. 2 ml of chloroform are then added, and the mixture is heated under reflux overnight. The mixture is allowed to cool to RT and poured into ethyl acetate/ice water. Solid sodium carbonate is then added. The phases are separated and the aqueous phase is washed with ethyl acetate. The organic phases are dried over sodium sulfate and concentrated. The residue is purified by column chromatography (silica gel 60, mobile phase: cyclohexane:methanol=4:1).

Provenance & Evidence