tert-Butyl 1H-indole-5carboxylate (0.800 g, 3.68 mmol), methyl 2-(3-cyano-4-fluorophenyl)acetate (0.593 g, 3.07 mmol), and potassium carbonate (0.509 g, 3.68 mmol) were combined in 15 mL of DMSO and the reaction mixture was stirred at 95° C. for 24 hours. Reaction was diluted with ethyl acetate washed twice with water, dried over magnesium sulfate and concentrated. Silica gel chromatography eluting with a gradient of 5% ethyl acetate/hexanes to 60% ethyl acetate/hexanes gave tert-butyl 1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylate (0.380 g, 0.973 mmol, 32%). MS (APCI)=390.9 (M+1).
