5-Bromo-2-chloro-3-nitropyridine → 4-Bromo-7-chloro-1H-pyrrolo(2,3-c)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-chloro-3-nitro-pyridine (7 g) in dry tetrahydrofuran (150 ml) at −70° C. under an atmosphere of nitrogen was added dropwise a solution of vinylmagnesium bromide (1.0M in tetrahydrofuran; 94.5 ml) over 1 h. The solution was stirred at −70° C. for 1 h and then quenched with saturated ammonium chloride (150 ml) and the aqueous was extracted twice with ethyl acetate. The combined organics were dried (MgSO4) and evaporated to give a deep red oil. The residue was triturated with diethyl ether (100 ml) and the solid was then filtered off, sucked dry then dried at 40° C. under vacuum to afford the title compound (1.75 g).

Provenance & Evidence