[I:1]I.[OH-].[K+].[CH3:5][O:6][P:7]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16](C(=O)C)[N:15]=[CH:14]2)(=[O:10])[O:8][CH3:9].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[CH3:5][O:6][P:7]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[C:14]2[I:1])(=[O:10])[O:8][CH3:9]814 mg (2 eq-3.206 mmol) of iodine and 180 mg (2 eq-3.206 mmol) of ground potassium hydroxide are added to a solution of 430 mg (1 eq-1.603 mmol) of (1-acetyl-1H-indazol-5-yl)phosphonic acid dimethyl ester in 20 ml of dimethylformamide. The medium is stirred at ambient temperature over a weekend. Another portion of 814 mg of iodine and 180 mg of potassium hydroxide are added to the reaction mixture, which is continued to stir for an additional period of 3 hours at ambient temperature. 20 ml of a saturated sodium thiosulfate solution are added and the medium is stirred for 10 minutes. The reaction mixture is washed with 40 ml of water. The aqueous phase is treated with 4 times 50 ml of ethyl acetate. The organic phase is dried over magnesium sulfate and then filtered and the solvent is evaporated off under reduced pressure in a rotary evaporator to obtain 458 mg of (3-iodo-1H-indazol-5-yl)phosphonic acid dimethyl ester.
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