Sodium Chloride → HCID 90416413, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence