Dimethylformamide → N-methyl-N'-(3-(octahydroindolizin-7-yl)-1H-indol-5-yl)urea

Participants

Reaction Steps

The trimethylsilyl isocyanate (288 mg, 2.50 mmol) was added to a solution of 3-(octahydroindolizin-7-yl)-5-amino-1H-indole (322 mg, 1.26 mmol) in 5 ml of dimethylformamide. The reaction was stirred at room temperature for 24 hours. TLC indicated consumption of starting material so the reaction was concentrated to give a purple foam which solidified. This material was chromatographed on a FLUORISIL™ column using 20% methanol in methylene chloride (ammonium hydroxide) as solvent to give 164 mg of product. (43.7%).

Provenance & Evidence