Triethylamine → ethyl 2-[3-[4-(2-naphthamido)benzyl]-2-methyl-1H-indol-1-yl]acetate

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Reaction Steps

In a dry reaction vessel, ethyl 2-[3-(4-aminobenzyl)-2-methyl-1H-indol-1-yl]acetate (1.644 g, 5.1 mmol) was added, and dissolved in 30 mL dichloromethane. Triethylamine (2.13 mL, 15.3 mmol) was added, and in an ice bath a dichloromethane solution dissolving 2-naphthoyl chloride (1.067 g, 5.6 mmol) was added slowly. After completion of dropwise addition, it was reacted in an ice bath for 1 h, and stirred at room temperature overnight. It was filtered. An aqueous solution of sodium bicarbonate was added, extracted with dichloromethane, rotate evaporated to dryness, chromatographed on a column to obtain a white solid 0.53 g, at a yield of 21.8%.

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