4-Toluenesulfonyl chloride → 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

To a suspension of 4-chloro-7-azaindole (2.32 g, 15.2 mmol) and p-toluenesulfonyl chloride (3.04 g, 15.96 mmol) in toluene (60 mL) and tetrabutylammonium sulfate (0.175 mL, 0.152 mmol, 50% solution in water) was added a solution of sodium hydroxide (0.913 g, 22.8 mmol) in water (36 mL). The biphasic mixture was stirred vigorously overnight, and was partitioned between ethyl acetate and brine. The aqueous layer was separated and extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-20% ethyl acetate in hexane) to provide the title compound. MS (DCI/NH3) m/z 307 (M+H)+.

Provenance & Evidence