Lithium Hydroxide → {3-[2-(3-Chlorobenzenesulfonyl)pyridin-3-ylmethyl]-5-fluoro-2-methylindol-1-yl}acetic acid

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A mixture of {3-[2-(3-chlorobenzenesulfonyl)pyridin-3-ylmethyl]-5-fluoro-2-methylindol-1-yl}acetic acid methyl ester (0.10 g) and tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.31 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure and the pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate and the combined extract was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume) to afford the title compound as a white solid (0.085 g).

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