6-(2-methoxyethoxy)-1H-indole → benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamate

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Reaction Steps

(E)-Benzyl 2-methyl-3-(2-nitroprop-1-enyl)phenylcarbamate (0.6849 g, 1.574 mmol) and 6-(2-methoxyethoxy)-1H-indole (0.602 g, 3.15 mmol) were dissolved in THF (50 mL), concentrated in vacuo, and melted at 140° C. for 12 h. After cooling to room temperature, the crude product was purified by flash chromatography using an ISCO 40 g column (solid loading) eluting with 20-75% EtOAc/hexane. Appropriate fractions were collected and concentrated in vacuo to give benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamate (0.4102 g, 0.793 mmol, 50.4% yield, mixture of 2 isomers) as a yellow oil, LC/MS (M+H)=518.12, 518.13.

Provenance & Evidence