1570075-58-9

Basic information

• Product Name: 9-(4-methylpyridin-2-yl)-9H-carbazole
• CAS NO: 1570075-58-9
• Molecular Weight: 258.323
• Mol File: 1570075-58-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 9-(4-methylpyridin-2-yl)-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(4-methylpyridin-2-yl)-9H-carbazole(1570075-58-9)
• EPA Substance Registry System: 9-(4-methylpyridin-2-yl)-9H-carbazole(1570075-58-9)

Safety Data

• Hazardous Substances Data: 1570075-58-9(Hazardous Substances Data)

Upstream product

• 4926-28-7 2-Bromo-4-picoline 
• 19933-06-3 4-methyl-N-phenyl-2-aminopyridine 

Relevant articles and documents

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.