2-Amino-5-methylpyridine → 6-Methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine

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[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=O.C(=O)(O)[O-].[Na+]>CCO>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)[N:1]=2)[CH:4]=1

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실험 절차

A mixture of 2-amino-5-picoline (0.88 g, 8.19 mmol) and 2-bromo-4′-nitroacetophenone (2.0 g, 8.19 mmol) in EtOH (50 ml) was heated under reflux for 17 h. The reaction mixture was allowed to cool and sodium bicarbonate (840 mg, 9.99 mmol) was added and heating was continued for 18 h. On cooling to room temperature, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (1:1 Hexane/EtOAc) to give the title compound (0.84 g, 40%) as a yellow solid.