Sodium hydride → 2-{2-[4-(1-[1,3]dioxolan-2-ylmethyl-1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid

Beteiligte Stoffe

Reaktionsschritte

0.02 g (0.42 mmol) of a dispersion of 60% NaH in mineral oil were added to a solution of 0.06 g (0.16 mmol) of 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid methyl ester prepared in step D in 1 mL of anhydrous DMF under an inert atmosphere. After stirring 30 minutes at room temperature, 0.04 mg (0.24 mmol) of 2-bromomethyl-[1,3]dioxolane were added and the mixture was stirred for 18 hours. The solvent was removed under reduced pressure and the crude mixture was dissolved in 1 mL of ethanol. 0.1 mL of 2N NaOH were added and the mixture was stirred at 60° C. for 3 hours. 0.1 mL of 2N HCl were added and the reaction mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the crude mixture was purified using a 500 mg Varian C18 chromatography column, affording 0.040 g (56% yield) of 2-{2-[4-(1-[1,3]dioxolan-2-ylmethyl-1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid.

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