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

Temperature

75 °C

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).

1. additionUpon completion of the addition
2. temperatureAfter cooling to RT
3. customthe reaction was quenched with water (25 mL)
4. temperatureThe mixture was then cooled to 0° C. and neutralised with addition of 6N sodium hydroxide solution
5. customThe ice bath was removed
6. stirringthe resulting slurry was stirred at RT for 3 hours
7. filtrationThe precipitate was filtered
8. washwashed with water

ORD record

ord-f723262d29874a93b34d4bb026084744

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877742B2