Dimethyl Sulfoxide → 6-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-beta-carboline

Participants

Reaction Steps

To a DMSO solution (4 ml) of 200 mg (0.755 mmol) of 6-chloro-7-fluoro-8-nitro-9H-β-carboline was added 1-methylpiperazine (226 mg, 2.26 mmol) and DIEA (400 mg, 3.09 mmol) via a syringe. The reaction was allowed to stir at RT overnight. Upon addition of water, an orange solid precipitated out. The solid was filtered, washed and dried to give 236 mg (91% yield) of the desired 6-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-β-carboline. 1H-NMR (300 MHz, DMSO-d6): δ 2.24 (s, 3H), 2.48 (m, 4H), 3.13 (m, 4H), 8.13 (d, 1H), 8.40 (d, 1H), 8.73 (s, 1H), 8.94 (s, 1H), 12.05 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.72 min. MS (M+H+): 346.

Provenance & Evidence