Potassium Carbonate → 5-Cyanomethoxy-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

Participants

Reaction Steps

α-Bromoacetonitrile (0.209 mL, 3.00 mmol, 1.0 eq.) was dissolved in dry acetonitrile (30 mL) and treated with 2-methyl-3-benzyloxycarbonyl-5-hydroxyindole (0.972 g, 3.46 mmol, 1.2 eq.) and potassium carbonate (0.690 g, 5.0 mmol, 1.7 eq.). The reaction was heated to reflux and followed by TLC (hexane/ethyl acetate 3/2). After 6 hours, the reaction was quenched with water and extracted with ethyl acetate. The resulting organic layers were concentrated, taken up in methylene chloride, and filtered. The filtrate was evaporated to afford a brown solid: 0.490 g (51% yield).

Provenance & Evidence