Water → 1-Propanesulfonamide, N-[3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-

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Reaction Steps

To aluminum trichloride (8.89 g, 66.7 mmol), 150 mL of dichloromethane was added under an atmosphere of nitrogen with the temperature maintained below 5° C. To this, 5-bromo-1H-pyrrolo[2,3-b]pyridine (8, 1.64 g, 8.34 mmol) in 20 mL of dichloromethane was added. The reaction was stirred for 60 minutes and 2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl chloride (7, 3.50 g, 11.8 mmol) in 20 mL of dichloromethane was added. The reaction was stirred for 6 hours, then warmed to room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum. The desired compound was isolated by silica gel column chromatography (dichloromethane/methanol 5%) to give a white solid (9, 1.2 g, 31.4%). MS(ESI) [M+H+]+=460.0, 462.0.

Provenance & Evidence