Patent ID: 6022980
Filing Date: 2000-02-08
Classification: C07D,C07F

Abstract:
A process for the synthesis of substituted 4- and 6-position melatonin compounds, comprising:a) substituting the 1-position of the melatonin in an appropriate solvent to produce the protected melatonin compound in which the only indole positions readily available for substitution are the 4- and 6- positions,b) mercurating the protected melatonin compound in an appropriate solvent with a mercuric salt to produce a mixture of the 4- and 6-organomercury products,c) treating the mixture of 4- and 6-organomercurated products in an appropriate solvent with a halide salt to provide a mixture of the corresponding 4- and 6-halomercury isomers,d) separating in an appropriate solvent the mixture of 4-halomercury and 6-halomercury isomers into the individual 4-halomercury and 6-halomercury isomers,e) treating, in an appropriate solvent, the individual 4-halomercurated and 6-halomercurated isomers with a halogenating agent to produce the corresponding isolated 4- and 6-halogenated compounds, andf) deprotecting the isolated 4- and 6-halogenated compounds in an appropriate solvent.