Cl[C:2]1[N:14]([CH3:15])[C:5]2=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]2[N:3]=1.[CH2:16]([S:18][C:19]1[NH:20][CH:21]=[CH:22][CH:23]=1)[CH3:17].[H-].[Na+].O>CN(C=O)C>[CH2:16]([S:18][C:19]1[N:20]([C:2]2[N:14]([CH3:15])[C:5]3=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]3[N:3]=2)[CH:21]=[CH:22][CH:23]=1)[CH3:17]A solution of 0.49 g of 2-chloro-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine in DMF (2 ml) was added to a mixture of 0.24 g of 2-ethylthio-1H-pyrrole, 0.11 g of sodium hydride (60% oil-based) and 3 ml of DMF, and the mixture was stirred at room temperature for 1.5 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous magnesiums sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.53 g of 2-(2-ethylthiopyrrol-1-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (23)).
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