HCID 86597543, compound → 3-(2-sulfanylethyl)-1H-indole-2-carboxylic acid

Participants

Reaction Steps

To a deoxygenated solution of 3-[2-(acetylthio)ethyl]-1H-indole-2-carboxylate (0.277 g, 1.0 mmol) in THF (5 mL) was added deoxygenated 0.5 N KOH (10 mL), and the mixture was stirred at room temperature under nitrogen for 20 hours. The volatile solvent was removed under reduced pressure and the resulting aqueous mixture was poured into a mixture of EtOAc/1 N HCl (10 mL/10 mL). The organic layer was dried over Na2SO4 and concentrated. The crude material was purified by silica gel chromatography (EtOAc/hexanes, 1/1) to give 0.150 g (0.68 mmol, 68% yield) of 3-(2-mercaptoethyl)-1H-indole-2-carboxylic acid as a white solid: 1H NMR (CDCl3) δ 1.49 (t, J=8.0 Hz, 1H), 2.91 (q, J=7.7 Hz, 2H), 3.48 (t, J=7.5 Hz, 2H), 7.19 (ddd, J=1.3, 6.6, and 8.1 Hz, 1H), 7.38 (t, J=7.4 Hz, 1H), 7.42 (d, J=8.1 Hz, 1H), 7.75 (d, J=8.1 Hz, 1H), 8.85 (s, 1H); 13C NMR (CDCl3) □ 25.4, 29.5, 112.0, 120.7, 121.1, 122.4, 124.7, 126.6, 127.9, 136.3, 167.0. Anal. Calcd. for C11H11NO2S: C, 59.71; H, 5.01; N, 6.33; S, 14.49. Found: C, 59.58; H, 5.07; N, 6.25; S, 14.28.

Provenance & Evidence