2-Bromo-3-nitropyridine → 7-Bromo-6-azaindole

Beteiligte Stoffe

Reaktionsschritte

A solution of 2-Bromo-3-nitropyridine (1 in Scheme 1, 2.0 g, 98%, 9.7 mmol) in dry THF (80 mL) was cooled to −78° C. Excess vinylmagnesium bromide (1.0 M in THF, 40 mL, 40 mmol) was added. The reaction mixture was stirred at −40˜−50° C. for 1 h before it was quenched with saturated NaHCO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc (3 times). The combined organic layers were dried over MgSO4, the dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash chromatography (EtOAc:n-hexane=1:2) to afford 2 (1.1 g, 60%).

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