S(=O)(=O)(O)O.[N:6]1([C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2N)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[N:7]1.Cl.N([O-])=O.[Na+].[I-:27].[K+]>O.C(OCC)(=O)C>[I:27][C:16]1[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=1[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[N:7]1Sulfuric acid (7.67 mL, 144 mmol) was added to a solution of 2-(1H-indazol-1-yl)aniline (1.771 g, 8.46 mmol) in concentrated HCl (2.030 mL, 25.4 mmol) at 0° C. The solution was stirred and after cooling back to 0° C., sodium nitrite (0.584 g, 8.46 mmol) in water (3.5 mL) was added dropwise. The reaction was stirred 40 min at 0° C. before potassium iodide (2.81 g, 16.93 mmol) in water (3.5 mL) was added dropwise and the solution was stirred at RT. After 1 h, the reaction is poured into ice with ethyl acetate and separated. The aqueous layer was extracted with EtOAc. The combined organic extracts were washed with 1N HCl, water, saturated sodium bicarbonate, 1N sodium sulfite, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material as an orange oil. The crude material was purified by silica gel chromatography by eluting with 1:4 EtOAc in hexane, to provide 1-(2-iodophenyl)-1H-indazole.
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