Sodium Sulfite → 5-Bromo-1-tosyl-1,2-dihydropyrrolo[2,3-b]pyridin-3-one

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Reaction Steps

5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde obtained by the method described in WO 2004/101565 (4.10 g) was dissolved in THF (100 ml). Triethylamine (3.05 ml) and p-toluenesulfonyl chloride (3.82 g) were added at room temperature and the mixture was stirred overnight. The reaction solvent was distilled off under reduced pressure and then diluted with ethyl acetate. After washing with water and brine in this order, the resulting organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was solidified with (dichloromethane-diethyl ether) and then collected by filtration to give 5-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (2.32 g). Further, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give 5-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (2.55 g). The resulting 5-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (2.83 g) was dissolved in methylene chloride (50 ml). 3-Chloroperbenzoic acid (2.13 g) was added under ice-cooling over 3 hours, and the mixture was stirred at room temperature for 2 hours. Thereafter, a 10% aqueous sodium sulfite solution and a saturated aqueous sodium bicarbonate solution were added to the reaction solution, followed by stirring overnight. The reaction solution was diluted with methylene chloride and the insoluble matter was removed by filtration, followed by extraction with methylene chloride three times. The resulting organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (0.18 g) as a pale red solid.

Provenance & Evidence