[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][CH:10]=2)[CH:7]=1.C(=O)(O)[O-].[Na+].[I:16]I>CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2[I:16])[CH:7]=1To a solution of 6-chloroimidazo[1,5-a]pyridine (417 mg, 2.73 mmol) in EtOH (5 mL) and water (2.4 mL) was added sodium bicarbonate (861 mg, 10.2 mmol) and iodine (832 mg, 3.28 mmol) and the mixture stirred at room temperature under N2. After 16 h the reaction mixture was quenched with sodium thiosulfate, then extracted into ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4), filtered, and concentrated. Purification of the filtrate by chromatography (silica, 20-60% ethyl acetate/hexanes) gave 6-chloro-1-iodoimidazo[1,5-a]pyridine (271 mg, 973 μmol, 36%) as a brown solid. MS (M+H)+=278.8; 1H NMR (CDCl3) δ: 8.10 (s, 1H), 8.0 (m, 1H), 7.30 (d, J=9.5 Hz, 1H), 6.76 (9.5 m, 1H).
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