1570075-45-4

Upstream product

• 591-50-4 iodobenzene 
• 10201-73-7 2-amino-4-methoxypyridine 
• 108-86-1 bromobenzene 
• 89488-29-9 2-bromo-4-methoxypyridine 
• 62-53-3 aniline 

Downstream Products

• 1570075-50-1 N-([1,1'-biphenyl]-2-yl)-4-methoxypyridin-2-amine 
• 578-95-0 10H-acridin-9-one 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Palladium-Catalyzed Late-Stage ortho-C-H Bond Aroylation of Anilines Using 4-Methoxy-2-pyridinyl as a Removable Directing Group

A synthetic methodology for the late-stage ortho-C-H bond aroylation of anilines with aryl aldehydes led to a variety of ortho-aroylated anilines by the use of palladium(II) acetate, tert-butyl hydroperoxide, and 1,4-dioxane as the catalyst, oxidant, and solvent, respectively, is presented. An N-phenylpyridin-2-amine palladacycle was isolated and characterized by X-ray crystallography. Controlled experiments, radical trapping experiments, and the experiments of the kinetic isotope effect were undertaken to support the proposed reaction mechanism. Syntheses of 2-aminobenzophenone and 9(10H)-acridanone based on the developed methodology were successfully demonstrated.

Ligand free copper-catalyzed N-arylation of heteroarylamines

An efficient protocol for ligand-free Cu-catalyzed N-arylation of heteroarylamines has been developed. With the use of 1% CuI, a wide range of aryl iodides and bromides coupled with heteroarylamines to afford the corresponding products in high yields. Further, this protocol is particularly suitable for reactions of the most hindered aryl iodides with 2-aminopyridines.

Palladium(II)-catalyzed direct ortho arylation of 4-methyl-N-phenylpyridin- 2-amines via C-H activation/C-C coupling and synthetic applications

The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of 1H NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.