Lithium Hydroxide → 6-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 2N lithium hydroxide (0.9 mL, 5 equiv, 1.8 mmole) is added to a solution of 6-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester (200 mg, 1.00 equiv, 0.36 mmole) in 1,4-dioxane (4 mL). The mixture is stirred at 90° C. for 24 h. The organic solvent is removed, HCl (1M) is added to adjust the pH to 3-4, and the resulting aqueous solution is extracted with dichloromethane. The organic layers are combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified via flash chromatography (12 g silica) eluting with a gradient of ethyl acetate in hexane (10% to 100%) to provide the title compound as a pale brown solid (168 mg, 86%). ES/MS m/z 542.0 (M+1).

Provenance & Evidence