Methyl iodide → HCID 9813602, compound

Temperature

25 °C

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.

1. customThe solvent is removed in vacuo
2. customthe remaining oil chromatographed with ethyl acetate-hexane as eluent
3. dissolutionThe product is dissolved in ethanol (10 ml)
4. dissolutionThe residue is dissolved in DMF (2 mL)
5. additionadded
6. filtrationthen filtered
7. customevaporated to dryness
8. dissolutiondissolved in ethanol
9. stirringstirred 1 h at 20° C
10. customThe solvent is removed
11. dissolutionthe compound dissolved in isopropanol-water (5:1)
12. additiontreated with 2 equivalents (w/w) of Dowex AG1-X8 ion exchange resin in the hydroxide form
13. customEvaporation of the solvent
14. customfollowed by crystallization

ORD record

ord-ec20d9375324447db849054f33be933b

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06730707B2