	US 12,331,020 B2
	Method of synthesizing indole compounds
Jason Ellis Hein, Vancouver (CA); Corey Sanz, Vancouver (CA); Shao-Kai Chen, Vancouver (CA); and Blessing Cao, Vancouver (CA)
Assigned to 1280225 B.C. LTD., Vancouver (CA)
Appl. No. 18/259,578
Filed by 1280225 B.C. LTD., Vancouver (CA)
PCT Filed Dec. 17, 2021, PCT No. PCT/CA2021/051833 § 371(c)(1), (2) Date Jun. 27, 2023, PCT Pub. No. WO2022/140844, PCT Pub. Date Jul. 7, 2022.
Claims priority of provisional application 63/253,961, filed on Oct. 8, 2021.
Claims priority of provisional application 63/133,056, filed on Dec. 31, 2020.
Prior Publication US 2024/0059653 A1, Feb. 22, 2024
Int. Cl. C07D 209/16 (2006.01); C07D 403/06 (2006.01); C07F 9/572 (2006.01)

CPC C07D 209/16 (2013.01) [C07D 403/06 (2013.01); C07F 9/5728 (2013.01)]

19 Claims

1. A method of synthesizing a tryptamine, comprising:

allyllating an indole compound comprising an indole ring and optionally a functional group on the indole ring to provide an α-indolepropene;

oxidizing the α-indolepropene to provide an indoleacetaldehyde; and

reductively aminating the indoleacetaldehyde to provide the tryptamine,

wherein oxidizing the α-indolepropene comprises:

oxidizing the α-indolepropene to provide an indole propyl diol; and

oxidizing the indole propyl diol to provide the indoleacetaldehyde; and

wherein oxidizing the indole propyl diol and reductively aminating the indoleacetaldehyde are effected without isolation of intermediates.