Sodium Sulfite → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-oxo-2-phenylethyl]amide

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Reaction Steps

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-(S)-hydroxy-2-phenylethyl]amide (Preparation 100, 304 mg, 0.661 mmol) in dry DCM (10 mL) was added Dess-Martin periodinane (342 mg, 0.806 mmol). After stirring for 3 h at room temperature alkaline sodium thiosulfate solution was added (5.4 g Na2SO3 dissolved in 20 mL saturated NaHCO3 solution) and the emulsion vigorously stirred for an additional 30 min. Ethyl acetate (150 ml) was added and the aqueous layer removed. The organic layer was washed with brine (50 ml), dried (MgSO4) and concentrated to a residue which was purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate: 50/50) to give the title compound as colourless solid. m/z (ES+)=458.34 [M+H]+; RT=4.32 min.

Provenance & Evidence