C([Mg][Br:4])C.I[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.Br[C:13]1[S:17][C:16]2=[C:18]([CH:21]=[O:22])N=[CH:20][N:15]2[CH:14]=1.[Cl-].[NH4+:24]>O1CCCC1>[Br:4][C:16]1[S:17][C:13]2=[C:14]([C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)[N:15]=[CH:20][N:24]2[C:18]=1[CH2:21][OH:22]
A 1 M tetrahydrofuran solution (0.9 ml) of ethylmagnesium bromide was added to a solution of 147 mg of 3-iodopyridine in 1 ml of tetrahydrofuran under an argon atmosphere, and the mixture was stirred at room temperature for 30 min. A solution of 149 mg of 2-bromo-7-formylimidazo[5,1-b]thiazole in 2 ml of tetrahydrofuran was added to the solution, and the mixture was stirred at that temperature for 2.5 hr. An aqueous saturated ammonium chloride solution was added to the reaction mixture to stop the reaction, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order and was then dried over magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by column chromatography on silica gel (ethyl acetate:methanol=4:1) to give 147 mg of 2-bromo-7-(pyridin-3-yl)hydroxymethylimidazo[5,1-b]thiazole.
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