Sodium Hydroxide → 3-(Cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylic acid

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The compound was prepared from ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate (Example 182) using the method described in Example 229, except 6N aqueous sodium hydroxide solution was used with tetrahydrofuran as a co-solvent. Flash chromatography of the residue over silica gel using 50% ethyl acetate/hexane gave the title compound (57%) as a pale yellow solid (mp=148-150° C). The product had: 1H NMR (300 MHz, acetone-d6) δ 11.70 (s, 1 H), 8.16 (d, 1 H), 7.70 (s, 1 H), 7.56-7.46 (m, 4 H), 7.35-7.27 (m, 2 H), 7.19-7.15 (m, 1 H), 5.98 (s, 2 H), 1.58-1.53 (m, 2 H), 1.33-1.28 (m, 2 H); mass spectroscopy gave MH+=372.1 (calcd exact mass for C21H16F3NH2=371.11).

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