6-Bromoindole → benzyl (3-(1-(6-bromo-1H-indol-3-yl)-2-nitropropyl)-2-methylphenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of (E)-benzyl (2-methyl-3-(2-nitroprop-1-en-1-yl)phenyl)carbamate (5.16 g, 15.8 mmol) and 6-bromo-1H-indole (6.20 g, 31.6 mmol) was heated neat at 140° C. overnight. The crude reaction mixture was purified by flash silica gel chromatography using a mixture of ethyl acetate in hexane (20%-35%-50%) to give benzyl (3-(1-(6-bromo-1H-indol-3-yl)-2-nitropropyl)-2-methylphenyl)carbamate (2.58 g, 4.94 mmol, 31% yield) as a burgundy oil/solid and as a 1:1 mixture of diastereomers.

Provenance & Evidence