Iodine → 6-Fluoro-1-iodoimidazo[1,5-A]pyridine
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C(=O)(O)[O-].[Na+].[F:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][CH:15]=2)[CH:12]=1.[I:16]I>O.CCO>[F:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][C:15]=2[I:16])[CH:12]=1C(=O)(O)[O-].[Na+].[F:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][CH:15]=2)[CH:12]=1.[I:16]I>O.CCO>[F:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][C:15]=2[I:16])[CH:12]=1To a solution of sodium bicarbonate (1.3 g, 15.4 mmol) in water (3.66 mL) was added 6-fluoroimidazo[1,5-a]pyridine (see Example 32, 560 mg, 4.11 mmol) in EtOH (7.31 mL) followed by iodine (1.46 g, 5.76 mmol) at room temperature. After 16 h another 800 mg of iodine was added. After a further 16 h the reaction mixture was quenched with sodium thiosulfate and diluted with ethyl acetate. The organic phase was washed with water and brine then dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (silica, ethyl acetate/hexane gradient). The product contained minor impurities and was used without further purification. MS (M+H)+=262.9; 1H NMR (CDCl3) δ: 8.14 (s, 1H), 7.90 (m, 1H), 7.35 (m, 1H), 6.77 (m, 1H).
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