Abstract: Described are methods of making pyranoindazole compounds comprising converting a pyranoindazole diol mixture to form a diastereomeric mixture of cyclic pyranoindazole carbonates, separating the mixture of cyclic pyranoindazole carbonates, and converting at least one of the separated diastereoisomeric cyclic pyranoindazole carbonates by hydrogenolysis. Also disclosed are intermediates useful for such and additional methods.

Abstract: Methods of making 1-alkylindazoles are described. The methods involve reacting a 2-alkylaminobenzonitrile with a nitrosating agent followed by reduction-cyclization of the resulting nitrosamine to form a 1-alkyl-3-aminoindazole. The 1-alkyl-3-aminoindazole can be deaminated to form a 1-alkylindazole which ultimately can be used to form desired indazoles which are preferably pharmaceutically active products. The process of the present invention further permits the formation of enantiomerically enriched or pure indazoles such as aminoalkyl indazoles.