[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[NH:5][CH:6]=1.CN(C=O)C.CC(C)([O-])C.[K+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[N:5]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:6]=1To a mixture of 4-chloro-1H-pyrrole-2-carboxylic acid (0.20 g) and DMF (2.0 mL) was added potassium tert-butoxide (0.31 g) under ice-cooling, followed by stirring at room temperature for 15 minutes. To the reaction mixture was added 1-bromomethyl-4-chlorobenzene (0.29 g) under ice-cooling, followed by stirring at room temperature for 14 hours. To the reaction mixture was added water at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-chloro-1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylic acid (0.06 g).
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