Nitrogen mustard hydrochloride → HCID 86663050, compound

Participants

Reaction Steps

A mixture of methyl 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (1.0 g, 3.1 mmol), 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride (1.20 g, 6.25 mmol) and sodium carbonate (1.66 g, 15 6 mmol) in t-BuOH (40 mL) was heated at reflux overnight. The reaction was partitioned between EtOAc and water and the organic phase was washed with sat. aq. NaHCO3 solution, water, and brine. After drying with sodium sulfate, the solvents were removed and silica gel chromatography (elution with 5% MeOH in DCM) afforded methyl 2-bromo-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (900 mg, 2.14 mmol, 69% yield). MS (ESI) m/z 405.14 (M+H); LCMS Ret Time: 1.995 min; Xbridge S10 4.6×50 mm column, 3 min gradient, 0-100% B, 4 mL/min. Solvent A: 95% MeOH—5% H2O—0.1% TFA; Solvent B: 5% MeOH—95% H2O—0.1% TFA.

Provenance & Evidence