2-Chloro-3-nitropyridine → 7-Chloro-1H-pyrrolo[2,3-c]pyridine

Participants

Reaction Steps

A solution of 2-chloro-3-nitropyridine (1 g, 6.3 mmol) in dry tetrahydrofuran (100 mL) was treated with vinyl magnesium bromide (60 mL, 60 mmol) at −78° C. in a drop-wise manner under inert atmosphere. The resulting reaction mixture was stirred at the same temperature for 2 hours followed by stirring at −20° C. for 8 hours. The reaction was quenched slowly with aqueous ammonium chloride solution (20 mL), extracted with ethyl acetate (3×50 mL) and the combined organic layer dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography using ethyl acetate and hexane gradient elution to afford 7-chloro-1H-pyrrolo[2,3-c]pyridine (0.350 g, 36.45%).

Provenance & Evidence