US 12,319,697 B2
Process for preparing imidazole derivatives
Matthieu Willot, Duesseldorf (DE); Ruediger Fischer, Pulheim (DE); Dominik Hager, Monheim (DE); Laura Hoffmeister, Duesseldorf (DE); Marc Mosrin, Monheim am Rhein (DE); and David Wilcke, Duesseldorf (DE)
Assigned to BAYER AKTIENGESELLSCHAFT, Leverkusen (DE)
Appl. No. 17/283,661
Filed by Bayer Aktiengesellschaft, Leverkusen (DE)
PCT Filed Oct. 9, 2019, PCT No. PCT/EP2019/077304
§ 371(c)(1), (2) Date Apr. 8, 2021,
PCT Pub. No. WO2020/074558, PCT Pub. Date Apr. 16, 2020.
Claims priority of application No. 18199885 (EP), filed on Oct. 11, 2018.
Prior Publication US 2022/0009930 A1, Jan. 13, 2022
Int. Cl. C07D 487/04 (2006.01); B01J 31/24 (2006.01); C07D 471/04 (2006.01)
CPC C07D 487/04 (2013.01) [B01J 31/2404 (2013.01); C07D 471/04 (2013.01); B01J 2531/824 (2013.01)] 12 Claims
 
1. A process for preparing a compound of formula (II)

OG Complex Work Unit Chemistry
wherein
Q represents a structural element Q2, Q3, or Q13,

OG Complex Work Unit Chemistry
where
R7 represents methyl, ethyl, n-propyl or isopropyl, and
A represents bromine, trifluoromethyl, pentafluoroethyl or trifluoromethylthio,
W represents S(O)nR8, where
R8 represents ethyl and
n represents 0 or 2,
V represents methyl and
Y represents hydrogen, bromine, cyclopropyl, para-chlorophenyl, cyanocyclopropyl-phenyl, 5-chlorothien-2-yl or 5-chloro-2-pyridine,
wherein, in a first process step a), a compound Q-H in which Q is as defined above is reacted with an organozinc base of formula (V)
(V) (TMP) ZnCI
to give a compound of formula (IIIa) or formula (IIIb)

OG Complex Work Unit Chemistry
(IIIa)

OG Complex Work Unit Chemistry
(IIIb),
wherein Q has the definition given above and R2 is chlorine,
and, in a second process step b), reacting the compound of formula (IIIa) or (IIIb) with a compound of formula (I)

OG Complex Work Unit Chemistry
wherein X represents iodine and V, W and Y each have the meanings mentioned above, in the presence of a catalyst, to give the compound of the formula (II).