Bisindolylmaleimide V → HCID 18505441, compound

Participants

Reaction Steps

Sodium hydride (60 to 72%, oily, 50 mg) was washed with pentane and then suspended into DMF (0.3 mL). A DMF solution (1.2 mL) of 2,3-bis(1H-indol-3-yl)-N-methylmaleimide (150 mg, 0.44 mmol) synthesized according to a known method (Tetrahedron, Vol. 44, p. 1887, 1988) was added thereto, and the whole was stirred at room temperature for 45 minutes. On the other hand, DMF (1.2 mL) was added at 0° C. to a mixture of (3-chloropropyl)dimethylamine hydrochloride (70 mg, 0.44 mmol) and sodium hydride (60 to 75%, oily, 18 mg) washed with pentane, and the whole was stirred for 5 minutes and then warmed to room temperature with standing. The supernatant was added to the solution of sodium salt of 2,3-bis(1H-indol-3-yl)-N-methylmaleimide. The resulting mixture was stirred at 40° C. for 1.5 hours, and then DMF was removed under reduced pressure. To the residue were added dichloromethane and saturated aqueous sodium chloride solution, and the organic layer was separated. The water layer was further extracted with dichloromethane. The resulting organic layers were combined and dried over sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by column chromatography over silica gel (chloroform saturated with ammonia:methanol=10:1) to obtain 2-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-N-methylmaleimide (77 mg, 41%) as dark red solids.

Provenance & Evidence