Carbon Dioxide → 7-Chloro-5-methyl-1H-pyrrolo[2,3-c]pyridine

Participants

Reaction Steps

Vinylmagnesium bromide solution (1 M in THF, 111 mL, 111 mmol) was added dropwise at −78° C. to a solution of 2-chloro-3-nitro-6-picoline (6.19 g, 35.2 mmol) in THF (200 mL). The dry ice cooling bath was replaced by an ice/NaCl cooling bath, and the reaction mixture was allowed to reach RT over 18 h, then the reaction mixture was carefully treated with 20% aq. ammonium chloride solution (210 mL). The reaction mixture was extracted with ethyl acetate, the organic layer was dried (MgSO4), and evaporated. Chromatography of the residue (SiO2, heptane/ethyl acetate gradient) afforded the title compound (2.58 g, 44%). Orange solid, MS (EI) 166.1 (100, M+).

Provenance & Evidence