Acetic Acid → 4-bromothieno[2,3-c]pyridine
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C(O)(=O)C.[Br:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]2[S:12][C:13](C([O-])=O)=[CH:14][C:7]=12>CN(C=O)C.C(OCC)(=O)C.C(=O)([O-])[O-].[Ag+2]>[Br:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]2[S:12][CH:13]=[CH:14][C:7]=12C(O)(=O)C.[Br:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]2[S:12][C:13](C([O-])=O)=[CH:14][C:7]=12>CN(C=O)C.C(OCC)(=O)C.C(=O)([O-])[O-].[Ag+2]>[Br:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]2[S:12][CH:13]=[CH:14][C:7]=12Silver carbonate (28 mg) and acetic acid (0.006 ml) were added to a solution of 4-bromothieno[2,3-c]pyridine-2-carboxylate obtained in the above-described Step 1 (258 mg) in DMF (2.0 ml), and the reaction solution was stirred at 120° C. for 24 hours. The reaction solution was diluted with ethyl acetate and washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain 4-bromothieno[2,3-c]pyridine.
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