[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[C:5]([O:7]CC)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27]([NH2:29])=[O:28])[CH:22]=1.O>CN(C=O)C>[C:27]([C:23]1[CH:22]=[C:21]([O:13][C:12]2[CH:11]=[CH:10][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[F:1])[CH:26]=[CH:25][N:24]=1)(=[O:28])[NH2:29]To a solution of ethyl 3-fluoro-4-hydroxybenzoate (2.0 mmol, 368 mg) in DMF (5 mL), were added cesium carbonate (Aldrich, 6.0 mmol, 1.95 g) and 4-chloropicolinamide (2.0 mmol, 312 mg). The reaction mixture was heated at 130° C. for 20 h. After cooling to room temperature, 5 mL of cold water was added. The aqueous solution was washed with EtOAc (2×20 mL), and neutralized with 1N HCl to pH 3-4. The precipitate that formed was collected by filtration, washed with water, and dried under vacuum to give the desired product (164 mg, 27% yield). MS(ESI+) m/z 277.32 (M+H)+.
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