2-Bromopyridine → 6-Chloro-3-nitro-2-(pyridine-2-carbonyl)indole

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Reaction Steps

To a solution of 2-bromopyridine (548 mg, 3.47 mmol) in diethyl ether (8 ml) cooled to −70° C. was added dropwise 1.66 M n-BuLi (2.1 ml in hexane). After stirring for 30 min, a solution of 6-chloro-2-(N-methoxy-N-methylamino)carbonyl-3-nitroindole (step 2, 328 mg, 1.16 mmol) in THF (8 ml) was added. The mixture was allowed to warm to ambient temperature and stirring continued for 5 h. Saturated ammonium chloride (20 ml) was then added and the mixture basified with saturated sodium bicarbonate (50 ml). The mixture was extracted with ethyl acetate (150 ml) and the extract was washed with brine (80 ml) and dried (Na2SO4). After removal of solvent by evaporation, the residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1:3) to afford 150 mg (43%) of the title compound.

Provenance & Evidence