[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16]C)=[CH:13][CH:14]=3)[C:9]([CH3:18])=[C:8]2[CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])=[CH:4][CH:3]=1.[CH2:28](S)C.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([CH3:18])=[C:8]2[CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([O:23][CH3:28])=[O:22])=[CH:4][CH:3]=1To a solution of 1.05 g (2.7 mmol) of 3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid (EP 166,591, Example 22) and 800 μL of ethanethiol (10 mmol) in 20 mL of CH2Cl2 at -20° C. was added in portions 2.17 g (16 mmol) of AlCl3. The reaction turned light orange and was stirred at room temperature overnight. In the morning, the reaction was completed (tlc) and it was poured into a solution of 1N HCl and extracted 3× with CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4), and filtered. The filtrate was evaporated and to the residual syrup (680 mg) was added 20 mL of Et2O followed by an ethereal solution of diazomethane. Evaporation of the solvent left the crude title compound which was used without further purification.
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