[CH3:1][O:2][CH:3](OC)[CH2:4]Br.Cl.C(=O)(O)[O-].[Na+].[I:14][C:15]1[CH:20]=[C:19](OC)[N:18]=[C:17]([NH2:23])[CH:16]=1>O.C(OCC)(=O)C>[I:14][C:15]1[CH:4]=[C:3]([O:2][CH3:1])[N:23]2[CH:20]=[CH:19][N:18]=[C:17]2[CH:16]=1
To a mixture of bromoacetaldehyde dimethylacetal (4.50 ml, 37.1 mmol) in water (126 ml) was added a 1M solution of hydrochloric acid (8.40 ml, 8.40 mmol). After 2.5 h the reaction mixture was heated to 80° C. resulting in a clear solution. After 40 minutes the reaction mixture was cooled to ambient temperature and sodium bicarbonate (3.83 g, 45.6 mmol) and 4-iodo-6-methoxypyridin-2-amine (5.25 g, 21.0 mmol) were added. After 16 hours the reaction mixture was diluted with ethyl acetate, washed with water, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (methanol/dichloromethane gradient) to give 7-iodo-5-methoxyimidazo[1,2-a]pyridine. LRMS (ESI) calculated for C8H8IN2O [M+H]+, 275.0 found 274.9.
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