US 12,215,063 B2
Method for preparing deuterated compound
Sunmin Kim, Daejeon (KR); Wanpyo Hong, Daejeon (KR); Woochul Lee, Daejeon (KR); Kyung Seok Jeong, Daejeon (KR); and Woo Han Kim, Daejeon (KR)
Assigned to LG CHEM, LTD., Seoul (KR)
Appl. No. 17/913,758
Filed by LG CHEM, LTD., Seoul (KR)
PCT Filed Mar. 23, 2021, PCT No. PCT/KR2021/003562
§ 371(c)(1), (2) Date Sep. 22, 2022,
PCT Pub. No. WO2021/210800, PCT Pub. Date Oct. 21, 2021.
Claims priority of application No. 10-2020-0046870 (KR), filed on Apr. 17, 2020.
Prior Publication US 2023/0331639 A1, Oct. 19, 2023
Int. Cl. C07B 59/00 (2006.01); C07C 1/32 (2006.01); C07C 15/28 (2006.01)
CPC C07B 59/001 (2013.01) [C07B 2200/05 (2013.01)] 8 Claims
OG exemplary drawing
 
1. A method for preparing a deuterated compound, the method comprising:
preparing a compound of Chemical Formula 2 by reacting a compound of Chemical Formula 1; a deuterium source; and a metal catalyst, and
forming a compound of Chemical Formula 3 reacting the compound of Chemical Formula 2,

OG Complex Work Unit Chemistry
wherein in Chemical Formulae 1 to 3,
R1 is hydrogen; a cyano group; a nitro group; a halogen group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
R2 is hydrogen or deuterium,
R3 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
D is deuterium,
r1 is an integer of 0 to 8, r1′ is an integer of 0 to 4, r1″ is an integer of 0 to 3, and when r1, r1′ and r1″ are 2 or greater, R1s are the same as or different from each other,
r3 is an integer of 0 to 8, and when r3 is 2 or greater, R3s are the same as or different from each other, and
n1 is an integer of 1 to 5, and n2 is an integer of 1 to 4.