Iodine → HCID 67517493, compound

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[C:11]([CH3:20])=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=1.[I:21]I>S([O-])([O-])(=O)=O.[Ag+2].CO>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:21])=[CH:4][C:3]=1[C:10]1[C:11]([CH3:20])=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=1

Participants

Procedure

Methyl 5-(2-fluoro-4-methoxyphenyl)-4-methylpyridine-2-carboxylate (190 mg, 0.690 mmol), silver sulfate (430 mg, 1.380 mmol), iodine (0.071 ml, 1.380 mmol) and MeOH (10 mL) were stirred at room temperature overnight. The crude mixture was filtered. The filtrate was concentrated in vacuo. The resulting pot residue was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 50 g cartridge). The column was eluted by an EtOAc/hexane mixture (0% to 40%). Related fractions were pooled and evaporated to afford a colorless oil as the titled compound. LCMS calc.=400.99. found=402.08 (M+H)+.