Short-RInChIKey=SA-FUHFF-UHFFFADPSC-OHIGKOFNMG-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

To a solution of methyl(triphenyl)phosphonium;iodide (1.37 g, 3.38 mmol, 1.15 equiv) in dry THF (30.0 mL), n-butyllithium solution (188 mg, 1.18 mL, 2.94 mmol, 2.50 M in hexane, 1.00 equiv) was dropwise added at -50 °C. After the addition, the reaction mixture was warmed to 0 °C. In another flask, 3-formyl-1H-indole-5-carbonitrile (500 mg, 2.94 mmol, 1.00 equiv) was dissolved in dry THF (10.0 mL) and sodium bis(trimethylsilyl)amide (539 mg, 2.94 mL, 2.94 mmol, 1.00 M in THF, 1.00 equiv) was added. The solution was added to the ylid dropwise at -30 °C. The reaction mixture was stirred for 1 hour at 21 °C, quenched with water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and filtered.