[CH3:1][C:2]1([CH3:11])[CH2:10][C:9]2[NH:8][N:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[OH-].[K+].[I:14]I>CN(C=O)C>[I:14][C:6]1[C:5]2[CH2:4][CH2:3][C:2]([CH3:11])([CH3:1])[CH2:10][C:9]=2[NH:8][N:7]=1To a solution of 6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole (0.50 g, 3.33 mmol) in DMF (8 mL) at room temperature was added powdered potassium hydroxide (560 mg, 10.0 mmol) and iodine (1.69 g, 6.66 mmol). The maroon reaction mixture was stirred at room temperature for 45 min then quenched with 10% aqueous Na2S2O3, diluted with water and extracted with EtOAc (2×). The combined organics were washed with water (3×), dried over MgSO4 and concentrated to afford 920 mg (99%) of 3-iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole as a light yellow waxy solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 2.44 (s, 2H), 2.35 (t, J=6.4 Hz, 2H), 1.55 (t, J=6.4 Hz, 2H), 1.01 (s, 6H).
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