Potassium Hydroxide → 8-[3-(3,4-Dimethoxy-phenyl)-indole-1-sulfonyl]-quinoline

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Reaction Steps

3-(3,4-Dimethoxy-phenyl)-indole 22 (70 mg, 0.28 mmol) was dissolved in methylene chloride (5.0 mL). Tetra-N-butylammonium bromide (3 mg, 0.01 mmol) and aqueous potassium hydroxide (50% wt/vol, 500 μL) were added. The reaction mixture was stirred for 5 minutes. 8-quinoline-sulfonyl chloride (89.5 mg, 0.39 mmol) was added and the reaction mixture was stirred for 2 hours. The product was extracted with 2 N lithium hydroxide and methylene chloride. The organic portion was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and purified by flash chromatography (ethyl acetate:hexanes 0%-50%). The appropriate fractions were combined and concentrated to provide 21, (76.1 mg, 90%). MS(ESI) [M+H+]+=445.0.

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