Sodium Sulfite → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-oxo-2-pyridin-3-ylethyl)amide

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Reaction Steps

To a solution of racemic 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-hydroxy-2-pyridin-3-ylethyl)amide (EXAMPLE 261, 80 mg, 0.253 mmol) in dry THF (20 mL) was added Dess-Martin periodinane (307 mg, 0.724 mmol). After stirring for 4 h at rt alkaline sodium thiosulfate solution was added (5.4 g Na2SO3 dissolved in 20 mL saturated NaHCO3 solution) and the emulsion was vigorously stirred for additional 30 min before further diluted with water (˜150 mL). Extraction with THF (4×50 mL), washing of the combined extracts with saturated sodium hydrogen carbonate (50 mL) and brine (50 mL) gave a solution which was concentrated after drying (MgSO4). Purification of the residue by flash chromatography on silica gel (eluent: DCM/methanol: 90/10) gave the title compound as off-white solid. m/z (ES+)=315.19 [M+H]+; RT=2.65 min.

Provenance & Evidence