N-bromobutanimide → HCID 20087998, compound

Participants

Reaction Steps

A mixture of 2,2,2-trichloroethyl 4-[3-(4-fluorophenyl)-1H-indol-1-yl]piperidine-1-carboxylate 10b (4.0 g), N-bromosuccinimid (1.5 g) and tetrachloromethane (60 ml) was refluxed for 2 h. The reaction mixture was cooled to room temperature and the precipitate was filtered off. Evaporation of the solvent afforded the crude 2,2,2-trichloroethyl 2-bromo-4-[3-(4-fluorophenyl)-1H-indol-1-yl]piperidine-1-carboxylate (4.4 g) as an oil which was used without further purification. A mixture of the crude 2-bromo-indole (4.4 g), zinc powder (4.4 g) and 90% acetic acid in water (150 ml) was heated at 40° C. for 30 min. The reaction mixture was filtered and the solvent evaporated in vacuo. To the remaining oil was added ethyl acetate (50 ml) and the thus obtained solution was washed successively with water, 4N aqueous NaOH and brine. Evaporation of the solvents afforded the title compound as an oil (2.9 g).

Provenance & Evidence