反应详情

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.

1. additionwas added
2. extractionExtraction with THF (4×50 mL)
3. washwashing of the combined extracts with saturated sodium hydrogen carbonate (50 mL) and brine (50 mL)
4. customgave a solution which
5. concentrationwas concentrated
6. dry with materialafter drying (MgSO4)
7. customPurification of the residue by flash chromatography on silica gel (eluent: DCM/methanol: 90/10)