METHOD OF SYNTHESIZING INDOLE COMPOUNDS

• Main Authors: CAO, Blessing, HEIN, Jason Ellis, SANZ, Corey, CHEN, Shao-kai (Patrick)
• Format: Patent
• Language: English; French; German
• Published: 08.11.2023
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

A method of synthesizing indole compounds. The method may include allyllating an indole compound, oxidizing the resulting α-indolepropene, and reductively aminating the resulting indoleacetaldehyde, providing a tryptamine. The indole compound may be substituted with a functional group on the indole ring or may be unsubstituted indole. The method may include substitution, oxidation or other derivatization of the indole ring of the indole compound, of tryptophan, of the tryptamine, or of intermediates. The method may include oxidizing tryptophan or a ring-substituted tryptophan analogue and reductively aminating the resulting indoleacetaldehyde, providing a tryptamine. The method may be applied in a telescoped approach without isolation of intermediates. The method may be applied to production of indoles, α-indolepropenes, indole propyl diols, indoleacetaldehydes and tryptamines. Compounds from each of these classes of compounds are also provided herein.