Benzenesulfonyl chloride → N-(5-bromopyridin-3-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-bromo-3-pyridinamine (2 g, 11.56 mmol), triethylamine (6.6 mL, 47.39 mmol) in dichloromethane (40 mL) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred for 15 min and then benzenesulfonyl chloride (3.21 mL, 23.69 mmol) was added slowly to give a brown solution. The reaction mixture was stirred for 2 h at room temperature. Diluted with dichloromethane and then washed with saturated aqueous sodium chloride solution, separated the organic layer, dried over sodium sulphate, concentrated under high vacuum, light yellow solid obtained. The solid was dissolved in methanol (20 mL), cooled to 0° C., added 10N aqueous sodium hydroxide (20 mL) solution. The reaction mixture was stirred for 1 h and then distilled out methanol completely, extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound MS (M+1): 315.2.

Provenance & Evidence