Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[OH:10][C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+].Cl>N1C=CC=CC=1.[Cu]I>[CH2:17]([O:16][C:14](=[O:15])[C:13]1[CH:19]=[CH:20][CH:21]=[C:11]([O:10][C:2]2[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[CH:12]=1)[CH3:18]A suspension of 5-bromo-2-methoxy-pyridine (5.4 g, 29 mmol), ethyl 3-hydroxybenzoate (4.0 g, 24 mmol), K2CO3 (4.3 g, 30 mmol), Cu powder (0.30 g, 4.8 mmol) and CuI (0.30 g, 1.56 mmol) in pyridine (25 ml) was refluxed for 18 h. The resulting mixture was mixed with 100 g of crushed ice, neutralized with 1N hydrochloric acid to pH 7.5 and extracted with ether. The extract was evaporated in vacuo, the obtained crude product was purified by column chromatography on silica (eluent hexanes-ethyl acetate 8:1) to afford 1.55 g (20%) of 3-(6-methoxy-pyridin-3-yloxy)-benzoic acid ethyl ester as colorless oil.
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