[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Mg+].[Br-].[CH3:13][O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=O.[Cl-].[NH4+].[CH2:26]([O:28]CC)C>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:26](=[O:28])[CH2:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[O:14][CH3:13])=[CH:2]1Indole (11.7 g, 100 mmol) was dissolved in diethylether (100 ml) under nitrogen atmosphere and cooled to 0° C. 3M MeMgBr solution (35 ml, 105 mmol) was added dropwise and allowed to stir at room temperature for 2 hours. The reaction mixture was cooled at 0° C. and a solution of 2-methoxybenzoyl chloride 2 (18.46 g, 100 mmol) in diethyl ether (100 ml) was added dropwise with vigorous stirring. The reaction mixture was then allowed to stir at room temperature for 2 hours. A solution of ammonium chloride (300 ml) was added to the reaction mixture and the resulting mixture was stirred at room temperature overnight. The solid that was formed was collected by filtration, washed with water and hexane then dried in a dessicator over phosphorous pentoxide to give 13 g (49%) of 1-(1H-indol-3-yl)-2-(2-methoxyphenyl)ethanone 3 as a cream solid.
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