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

Temperature

75 °C

To a suspension of the 4-bromo-1H-pyrrolo[2,3-b]pyridine 7-oxide (27 mmol) in N,N-dimethylformamide (57 mL) at 50° C. was added methanesulfonyl chloride (67.5 mmol) under nitrogen. Upon completion of the addition, the reaction was stirred at 75° C. for 1 hour. The reaction was cooled to room temperature and quenched with water (60 mL). Then, it was cooled to 5° C. and 6N sodium hydroxide solution was added to raise the pH to 7. The ice bath was removed and the resulting slurry was stirred at room temperature for 3 h. The precipitate was filtered, washed with water (50 mL), and dried under high vacuum to give the title product as a white solid (89%). ESMS [M+H]+: 231.0

1. additionUpon completion of the addition
2. temperatureThe reaction was cooled to room temperature
3. customquenched with water (60 mL)
4. temperatureThen, it was cooled to 5° C.
5. addition6N sodium hydroxide solution was added
6. temperatureto raise the pH to 7
7. customThe ice bath was removed
8. stirringthe resulting slurry was stirred at room temperature for 3 h
9. filtrationThe precipitate was filtered
10. washwashed with water (50 mL)
11. customdried under high vacuum

ORD record

ord-589cf7b4436b41e4ae624d07d76190f4

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07419988B2