Hydrochloric Acid → HCID 68444970, compound

Participants

Reaction Steps

Ethyl 5-bromo-6-nitro-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxylate (256 mg, 0.55 mmol, 1.0 equiv) was suspended in 10 mL of absolute ethanol. 1.5 mL of concentrated aqueous HCl was added, followed Zn dust (362 mg, 5.5 mmol, 10 equiv), and the reaction was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water, which was extracted three times with ethyl acetate. The combined organic layers were washed once with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30% ethyl acetate/dichloromethane) provided the titled compound. Proton NMR for the product was consistent with the titled compound. 1H NMR (500 MHz, DMSO-d6): δ 12.38 (s, 1H), 8.15 (br s, 1H), 8.05 (br s, 1H), 7.91 (s, 1H), 6.94 (s, 1H), 3.62 (m, 4H), 2.87 (m, 4H) ppm. ESI+MS: 431.2 [M+H]+.

Provenance & Evidence