Br[CH:2](Br)[C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1.[C:14]([O-:17])(O)=O.[Na+].[Na+].[Cl-].[CH3:21][OH:22]>C(OC)(OC)OC.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:21][O:22][CH:2]([O:17][CH3:14])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1
To a solution of methyl 5-(dibromomethyl)pyridine-2-carboxylate (927 mg, 3.00 mmol) in methanol (10 ml) and trimethyl orthoformate (2 ml) was added a solution AgNO3 (1.12 g, 6.6 mmol) in methanol (20 ml) over 15 minutes. After refluxing the reaction for 1 hour, it was cooled and poured into a solution of NaHCO3 (0.84 g, 10 mmol) in water (50 ml) containing a small amount of NaCl. The thick slurry was filtered through a 25-50 micron frit, and the filtrate concentrated to 10 ml and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried (MgSO4), filtered and concentrated to give title product (550 mg, 96%).
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