1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylic acid (0.020 g, 0.078 mmol, triethylamine (0.013 mL, 0.090 mmol) and oxalyl chloride (0.010 g, 0.079 mmol) was combined in 1 mL of DCM and 1 drop of DMF was added. The reaction mixture was stirred at ambient temperature for 30 minutes. To the reaction mixture was added 2-(2,4-dichlorophenyl)ethanamine.The reaction mixture was stirred for 1 hour then loaded onto a silica gel column. The product was eluted with solvent system of 5% EtOAc/Hexanes to 100% EtOAc to provide methyl 2-(4-(5-((2,4-dichlorophenethyl)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetate (0.170 g, 0.034 mmol). MS(APCI)=506.1 (M+1).
