[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]=[CH:16][O:15][CH:14]=2)=[CH:9][CH:8]=1.[C:18]([O-:21])([O-])=O.[Na+].[Na+].BrBr.[CH3:26][OH:27]>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:26][O:27][CH:14]1[C:13]([C:10]2[CH:9]=[CH:8][C:7]([C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:12][CH:11]=2)=[CH:17][CH:16]([O:21][CH3:18])[O:15]1To a slurry of 3-[4-(pyrimidin-2-yl)phenyl]furan and Na2CO3 (46 mg, 0.44 mmol) in methanol (0.8 mL) and benzene (0.8 mL) at −10° C. was added bromine (22 μL, 0.41 mmol) dropwise. The reaction mixture was stirred at −10° C. for 1 h, diluted with ethyl acetate, filtered, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 2:1 hexanes/ethyl acetate) gave 95 mg (75%) of the title compound. MS 285 (M+H)+.
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