Triethylamine → N-[3-(1-Methylpiperdin-4-yl)indol-5-yl]-N'-[4-(pyridin-4-yl)naphth-1-yl]-urea

Participants

Reaction Steps

To a stirred solution of triphosgene (0.09 g, 0.31 mmole) in dichloromethane (15 ml) under argon, was added dropwise a solution of 4-(pyridin-4-yl)naphth-1-ylamine (D3, 0.17 g, 0.77 mmole) and triethylamine (0.12 ml, 0.83 mmole) in dichloromethane (10 ml). The mixture was then stirred at room temperature for 20 minutes, then a solution of 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole (D2, 0.15 g, 0.66 mmole) in dichloromethane (10 ml) was slowly added. After stirring the mixture for 1 hour, dilute potassium carbonate solution (10 ml) was added. The precipitated solid mass was collected and purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH/NH4OH (100:10:1) to afford the title compound as a buff powder (0.14 g).

Provenance & Evidence