[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[C:13]([O:21]C)=[N:14][C:15]([CH3:20])=[C:16]([CH2:18][CH3:19])[CH:17]=1.[B].C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCC>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[C:13](=[O:21])[NH:14][C:15]([CH3:20])=[C:16]([CH2:18][CH3:19])[CH:17]=1
3[(Benzoxazol-2-yl)methoxy]-2-methoxy-5-ethyl-6-methylpyridine (140 mg, 0.47 mmol) was dissolved in methylene chloride (5 ml) and cooled in an ice bath under an atmosphere of nitrogen. 1M Boron tribomide (2.3 mL, 2.3 mmol) in hexane was added to this solution and the reaction mixture was allowed to warm to room temperature over a 0.75 hour period. This mixture was re-cooled in an ice bath and saturated aqueous NaHCO3 (5 mL) was added to quench the reaction. The methylene chloride layer was dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether to give 69 mg of crude product. Recrystallization from methanol yielded 60 mg (45%), m.p. 198°-200° C.
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