Sodium Chloride → HCID 90416413, compound

Temperature

0 °C

Sodium hydride (60% dispersion in oil, 1.45 g, 36.3 mmol) was added portionwise to a 0° C. solution of 5-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine (CAS 1198096-48-8) (4.2 g, 18.14 mmol) and tetrahydrofuran (42 mL). After 15 minutes at 0° C. iodomethane (1.7 mL, 27.2 mmol) was added. The reaction mixture was stirred at 0° C. for 30 minutes and at ambient temperature for 2 hours. The reaction mixture was cooled to 0° C. and 30 mL saturated aqueous ammonium chloride solution was added, followed by addition of saturated aqueous sodium chloride. The mixture was extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to afford 5 g yellow solid. The crude product was purified by flash chromatography (silica gel, 2-20% ethyl acetate in heptanes) to provide 3.7 g (84%) of the title compound.

1. temperatureThe reaction mixture was cooled to 0° C.
2. extractionThe mixture was extracted with ethyl acetate
3. extractionThe organic extract
4. washwas washed with saturated aqueous sodium chloride
5. dry with materialdried (anhydrous sodium sulfate)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-9d4a8e7f2311467d988d4125aec7da6a

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321764B2