[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[CH:7]=1.N1C=CN=C1.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][O:12][Si:22]([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23])[N:10]=2)[CH:7]=1To solution of (6-bromoimidazo[1,2-a]pyridin-2-yl)methanol (3.21 g, 14.13 mmol) in DCM (50 mL) was added imidazole (1.30 g, 19.09 mmol) followed by TBSCl (2.60 g, 17.25 mmol). Reaction mixture was stirred at room temperature for 30 min then was diluted with DCM (50 mL) and washed with H2O (50 mL). Organic phase was washed with NaCl (aqueous saturated, 50 mL) and dried over Na2SO4. Solvent was concentrated and residue purified by column chromatography using EtOAc/hexanes (gradient 0-50%) to afford 6-bromo-2-((tert-butyldimethylsilyloxy)methyl)imidazo[1,2-a]pyridine (3.32 g) in 69% yield as pale yellow solid.
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