N,N-Diethylethylenediamine → 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrole-1-carboxylic acid (2-diethylamino-ethyl)-amide

Beteiligte Stoffe

Reaktionsschritte

To a cold solution of 3-(1-Methyl-3-indolyl)-4-(1-methyl-6-nitro-3-indolyl)-1H-pyrrole-2,5-dione (200 mg, 0.5 mmol) (see Davis U.S. Pat. No. 5,057,614) in THF (7 mL) was added dropwise, lithium bis(trimethylsilyl)amide (0.55 mmol, 0.55 mL, 1 M in THF). The resulting red suspension was stirred for 15 min. Bis(p-nitrophenyl)carbonate (213 mg, 0.7 mmol) was added. The solution was stirred at 0° C. for 0.5 h. Diethylaminoethylamine (69.7 mg, 0.6 mmol) in THF (2 mL) was added, and stirring was continued for 2 h. The solvent was evaporated and the residue was purified by flash chromatography to give 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrole-1-carboxylic acid (2-diethylamino-ethyl)-amide (28 mg, 10%).

Herkunft & Nachweise