Methanesulfonyl chloride → 4-Bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-bromo-1H-pyrrolo[2,3-b]pyridine 7-oxide (D29) (1.95 g, 9.15 mmol) in DMF (15 mL) at 50° C. was added methanesulfonyl chloride (1.783 mL, 22.88 mmol). Upon completion of the addition, the mixture was stirred at 75° C. for 1 hour. After cooling to RT, the reaction was quenched with water (25 mL). The mixture was then cooled to 0° C. and neutralised with addition of 6N sodium hydroxide solution. The ice bath was removed and the resulting slurry was stirred at RT for 3 hours. The precipitate was filtered and washed with water to give the title compound (1.88 g). This was used in the next step without further purification. LCMS (A): m/z (M+H)+ 233, C7H4BrClN2 requires 232 (acidic).

Provenance & Evidence