Method of preparing benzoimidazole derivatives

A method of preparing a benzimidazole compound, comprising the steps of:

• 1) reacting a compound represented by Chemical Formula 7 below with a compound represented by Chemical Formula 3 below in the presence of a palladium catalyst to prepare an intermediate compound, wherein said intermediate compound is selected from the group consisting of:
• 4-(3-chloropyridin-2-yl)-1-naphthaldehyde,
• N-(3-fluoro-4′-formylbiphenyl-4-yl)methane sulfoneamide,
• 4-(3-(trifluoromethyl)pyridin-2-yl)benzaldehyde,
• 3-(trifluoromethyl)-2,3′-bipyridine-6′-carbaldehyde, and
• 3-chloro-2,3′-bipyridine-6′-carbaldehyde;
• and
• 2) reacting the intermediate compound with a compound represented by Chemical Formula 6 below, to yield the benzimidazole compound, wherein the step 3) is performed using 1,4-benzoquinone as an additive and 1,4-dioxane or acetonitrile as a solvent,
• wherein said benzimidazole compound is selected from the group consisting of:
• 6-tert-butyl-2-(4-(3-chloropyridin-2-yl)naphthalen-1-yl)-1H-benzo[d]imidazole,
• N-(4′-(4,6-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-3-fluorobiphenyl-4-yl)methanesulfoneamide,
• 4-bromo-6-(trifluoromethyl)-2-(4-(3-(trifluoromethyl)pyridin-2-yl)phenyl)-1H-benzo[d]imidazole,
• 6-bromo-2-(4-(3-(trifluoromethyl)pyridin-2-yl)phenyl)-1H-imidazo[4,5-b]pyridine,
• 6-(trifluoromethyl)-2-(3-(trifluoromethyl)-2,3′-bipyridin-6′-yl)-1H-benzo[d]imidazole,
• 6-bromo-2-(3-(trifluoromethyl)-2,3′-bipyridin-6′-yl)-1H-benzo[d]imidazole,
• 6-bromo-2-(3-(trifluoromethyl)-2,3′-bipyridin-6′-yl)-1H-imidazo[4,5-b]pyridine,
• 4-(2-(3-(trifluoromethyl)-2,3′-bipyridin-6′-yl)-3H-benzo[d]imidazol-5-yl)morpholine,
• 4-chloro-2-(3-chloro-2,3′-bipyridin-6′-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazole, and
• 2-(3-chloro-2,3′-bipyridin-6′-yl)-4,6-bis(trifluoromethyl)-1H-benzo[d]imidazole;
• wherein M is B(OH)2, B(i-Pr)2, Sn(CH3)3, or SnBu3,
• X is CH or N,
• Y is CR5 or N,
• R1 is
• R2 and R3 each are hydrogen or R2 and R3 together form a benzene ring,
• R4 is Br, tert-butyl, trifluoromethyl, or morpholino,
• R5 is hydrogen, Cl, Br, or trifluoromethyl, and
• R6 is hydrogen, Cl, or trifluoromethyl.

Any one compound selected from the group consisting of:

• 4-(3-chloropyridin-2-yl)-1-naphthaldehyde,
• N-(3-fluoro-4′-formylbiphenyl-4-yl)methane sulfoneamide,
• 3-(trifluoromethyl)-2,3′-bipyridine-6′-carbaldehyde, and
• 3-chloro-2,3′-bipyridine-6′-carbaldehyde.