Back to results
US 2025/0177538 A1Published application
Methods for synthesizing deuterated formylindoles
AssigneeArizona Board of Regents on Behalf of the University of Arizona
InventorWei Wang
Life of this patent
Estimating the term…
Abstract
Exemplary materials, methods and techniques disclosed and contemplated herein generally relate to the photochemical synthesis of various deuterated 3-formyl indoles using deuterated glyoxylic acid (CDOCO2D).
Claims28
A method for preparing a deuterated compound of formula (I), or a salt thereof,
- wherein:
- RX is halogen, C1-4alkyl, C1-2haloalkyl, Ra, —NO2, —CN, —CO2C1-4alkyl, —C(O)C1-4alkyl, —C(O)H, —OC1-3alkylene-Ra, —C1-3alkylene-Ra, -L1-A1, or -L2-A2;
- Ra is C3-4cycloalkyl, —OC1-4alkyl, —OC1-2haloalkyl, —OC3-4cycloalkyl, or phenyl, wherein, at each occurrence, the phenyl is optionally substituted with 1-2 substituents selected from the group consisting of halogen, C1-4alkyl, C1-2haloalkyl, —NO2, —CN, —OC1-4alkyl, —OC1-2haloalkyl, or —OC3-4cycloalkyl;
- RY is hydrogen, C1-4alkyl, or an amine protecting group;
- RZ is hydrogen, C1-4alkyl, C2-4alkenyl, or unsubstituted phenyl;
- L1 is —C1-3alkylene- or —OC1-3alkylene-;
- A1 is a drug moiety;
- wherein A1 is linked to L1 by
- L2 is —NH—;
- A2 is a drug moiety;
- wherein A2 is linked to L2 by:
- and
- n is 0, 1, or 2;
- the method comprising:
- mixing D-CO2D with a compound of formula (II),
- in an organic solvent to form a mixture;
- and
- exposing the mixture of (i) to light, thereby producing the deuterated compound of formula (I), or a salt thereof.
15 more elements
A deuterated compound of formula (I), or a salt thereof,
- wherein:
- Rx is halogen, C1-4alkyl, C1-2haloalkyl, Ra, —NO2, —CN, —CO2C1-4alkyl, —C(O)C1-4alkyl, —C(O)H, —OC1-3alkylene-Ra, —C1-3alkylene-Ra, -L1-A1, or -L2-A2;
- Ra is C3-4cycloalkyl, —OC1-4alkyl, —OC1-2haloalkyl, —OC3-4cycloalkyl, or phenyl, wherein, at each occurrence, the phenyl is optionally substituted with 1-2 substituents selected from the group consisting of halogen, C1-4alkyl, C1-2haloalkyl, —NO2, —CN, —OC1-4alkyl, —OC1-2haloalkyl, or —OC3-4cycloalkyl;
- RY is hydrogen, C1-4alkyl, or an amine protecting group;
- RZ is hydrogen, C1-4alkyl, C2-4alkenyl, or unsubstituted phenyl;
- L1 is —C1-3alkylene- or —OC1-3alkylene-;
- A1 is a drug moiety;
- wherein A1 is linked to L1 by
- L2 is —NH—;
- A2 is a drug moiety;
- wherein A2 is linked to L2 by:
- and
- n is 0, 1, or 2.
10 more elements
Dependencies are inferred from the claim text.