Hydrochloric Acid → HCID 10125929, compound

Participants

Reaction Steps

To a solution of 3-(2-acetylsulfanyl-ethyl)-1-(3-methoxycarbonyl-phenyl)-1H-indole-2-carboxylic acid methyl ester (0.32 g, 0.73 mmol) in THF (10 mL) was dropwise added 0.5 N KOH (10 mL) and the resulting mixture was stirred at room temperature overnight. The reaction acidified with 3 N HCl and the resulting white precipitate was washed with H2O and dried under vacuum to give 0.22 g of a white solid (85% yield over 2 steps): 1H NMR (DMSO-d6, 300 MHz) δ 2.81 (t, J=6 Hz, 2H), 3.37 (t, J=6 Hz, 2H), 7.02 (d, J=9 Hz, 1H), 7.19 (t, J=6 Hz, 1H), 7.28 (t, J=6 Hz, 1H), 7.63 (m, 2H), 7.77 (s, 1H), 7.83 (d, J=9 Hz, 1H), 8.01 (d, J=9 Hz, 1H); 13C NMR (DMSO-d6, 300 MHz) δ 25.18, 29.62, 111.11, 121.26, 123.93, 126.18, 127.13, 127.28, 128.35, 129.10, 129.86, 132.24, 138.93, 139.48, 162.78, 167.07. Anal. Calcd for C18H15NO4S: C, 63.33; H, 4.43; N, 4.10; S, 9.39. Found: C, 63.03; H, 4.6; N, 4.09; S, 9.16.

Provenance & Evidence