Methyl iodide → HCID 9813602, compound

Participants

Reaction Conditions

Reaction Steps

N-[2-(5-Nitro-1H-indol-3-yl)-ethyl]-acetamide (0.6 mmol) is taken into acetonitrile (1 mL) and stirred with a catalytic amount of DMAP and di-t-butyl dicarbonate (0.7 mmol) for 1 h. The solvent is removed in vacuo and the remaining oil chromatographed with ethyl acetate-hexane as eluent. The product is dissolved in ethanol (10 ml) and hydrogenated as above. The residue is dissolved in DMF (2 mL), and diisopropylethylamine (1.4 mmol) followed by methyl iodide (1.4 mmol) added. The mixture is stirred 3 h at 25° C. then filtered, evaporated to dryness, dissolved in ethanol and decolorized with activated charcoal. The residue is dissolved in trifluoroacetic acid with 1 equivalent of thiophenol and stirred 1 h at 20° C. The solvent is removed, the compound dissolved in isopropanol-water (5:1) and treated with 2 equivalents (w/w) of Dowex AG1-X8 ion exchange resin in the hydroxide form. Evaporation of the solvent followed by crystallization affords the title compound.

Provenance & Evidence