[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10]([C:12]1[N:13]([CH2:26][C:27]#[N:28])[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:16][CH:15]=2)=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(OCC)C>[F:23][C:22]([F:24])([F:25])[O:21][C:17]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:26][CH2:27][NH:28][CH2:10][C:12]3=[CH:20][C:19]=2[CH:18]=1To a suspension of Lithium Aluminium Hydride (0.68 g) in diethylether (70 mL) was added portionwise 1-cyanomethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid ethyl ester (2.28 g). The reaction mixture was then stirred for 16 hours at reflux. The solution was then slowly poured into a saturated solution of sodium-potassium tartrate. The mixture was then extracted with ethyl acetate 3 times. The combined organic phases were then washed with brine, dried with magnesium sulfate, concentrated in vacuo and purified by column chromatography to yield the desired compound (0.83 g, 45%).
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