6-Bromoindole → Benzyl 3-(1-(6-bromo-1H-indol-3-yl)-2-nitroethyl)-2-methylphenylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-1H-indole (2.82 g, 14.41 mmol) and (E)-benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate (3.0 g, 9.61 mmol) was dissolved in THF (50 mL) and NMP (0.5 mL). The THF was removed under vacuum, and the residue was heated at 120° C. for 16 hr and then at 125° C. for 6 hr. Upon cooling to room temperature, the mixture was dissolved in THF (50 mL). The resulting solution was diluted with ethyl acetate (250 mL), washed with water (3×80 mL) and brine (60 mL), and dried over anhydrous MgSO4. The desired product (3.00 g, 5.90 mmol, 61.4% yield) was isolated as a beige solid by ISCO (300 g silica gel, 25-60 ethyl acetate/hexane).

Provenance & Evidence