Potassium Carbonate → 2-Methyl-5-(1-methyl-piperidin-3-ylmethoxy)-1H-indole-3-carboxylic Acid Benzyl Ester

Participants

Reaction Steps

Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester (0.753 g, 2.66 mmol, 1.0 eq) was dissolved in dry acetonitrile (30 mL), and treated with 2-methyl-3-benzyloxycarbonyl-5-hydroxyindole (0.759 g, 2.70 mmol, 1 eq) and potassium carbonate (0.690 g, 5 mmol, 2.0 eq.). The reaction was heated to reflux and followed by TLC (ethyl acetate/methanol/triethylamine 87/10/3). After 96 hours, the reaction was loaded directly on silica gel and chromatographed (ethyl acetate/methanol/triethylamine 87/10/3) to afford a white solid: 0.237 g (24% yield). This was converted to the corresponding hydrochloride salt: LC/MS (ESI+) 393 (M+1), Anal. (C24H28N2O3.HCl.0.6H2O) C, H, N.

Provenance & Evidence