US 11,993,592 B2
Phebox ligands and methods of making same
Alan S. Goldman, Piscataway, NJ (US); and Thomas R. Dugan, Piscataway, NJ (US)
Assigned to Rutgers, The State University of New Jersey, New Brunswick, NJ (US)
Filed by Rutgers, The State University of New Jersey, New Brunswick, NJ (US)
Filed on Sep. 7, 2022, as Appl. No. 17/939,047.
Application 17/939,047 is a continuation of application No. 17/209,850, filed on Mar. 23, 2021, granted, now 11,465,996.
Claims priority of provisional application 62/993,154, filed on Mar. 23, 2020.
Prior Publication US 2023/0022558 A1, Jan. 26, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 413/10 (2006.01)
CPC C07D 413/10 (2013.01) 12 Claims
 
1. A method of making the compound of formula (I), or a salt or solvate thereof:

OG Complex Work Unit Chemistry
wherein:
R1 and R2 are each CH3, or R1 and R2 taken together are —(CH2)4— or —(CH2)5—;
R3 is selected from the group consisting of CF3, CF2CF3, CN, and NO2;
R4 is selected from the group consisting of CF3, CF2CF3, CN, and NO2; with the provisos that:
if one of R3 and R4 is CN, then the other is CF2CF3 or NO2;
if one of R3 and R4 is NO2, then the other is CF3, CF2CF3, or CN;
R5 is selected from the group consisting of H, CF3, CF2CF3, CN, and NO2; and
E is CH,
the method comprising:
converting

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 into

OG Complex Work Unit Chemistry
 and
contacting

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 with

OG Complex Work Unit Chemistry
 to provide the compound of formula (I),
wherein in the compound of formula (V):
R3 is selected from the group consisting of CF3, CF2CF3, CN, and NO2;
R4 is selected from the group consisting of CF3, CF2CF3, CN, and NO2; and
with the provisos that
if one of R3 and R4 is CN, then the other is CF2CF3 or NO2;
if one of R3 and R4 is NO2, then the other is CF3, CF2CF3, or CN.