In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Cu-Catalyzed Couplings of Heteroaryl Primary Amines and (Hetero)aryl Bromides with 6-Hydroxypicolinamide Ligands, published in 2019-08-16, which mentions a compound: 87488-84-4, mainly applied to copper hydroxypicolinamide catalyst coupling heteroaryl primary amine aryl bromide, Recommanded Product: 1-(2-Bromophenyl)-1H-pyrazole.
A family of 6-hydroxypicolinamide ligands have been identified as effective supporting ligands for Cu-catalyzed couplings of heteroaryl bromides and chlorides with heteroaryl primary amines. The C-N couplings are carried out at 80-120° in DMSO or sulfolane using K2CO3 or K3PO4 as the base with 2-10 mol% CuI and supporting ligand. The strength of the base was found to have an impact on the chemoselectivity and rate. The use of K2CO3 as the base enabled selective C-N coupling of aryl bromides over aryl chlorides with 2-5 mol% Cu at 80-120°. With K3PO4 as the base, aryl chlorides are capable of undergoing C-N coupling, though 5-10 mol% Cu is required at 120-130°. Members of the ligand family are straightforward to prepare in one step from 6-hydroxypicolinic acid and the corresponding anilines.
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Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem