Step 3: 6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole (0.50 g, 3.33 mmol) was dissolved in DMF (8 mL) at room temperature and powdered potassium hydroxide (560 mg, 10.0 mmol) and iodine (1.69 g, 6.66 mmol) were added sequentially. The reaction mixture was stirred for 45 min until the color changed to maroon. Upon completion of the reaction, the reaction was quenched with 10% Na2S2O3 aqueous solution, diluted with water and extracted with EtOAc (2×). The organic phases were combined, washed with water (3×), dried over MgSO4 and concentrated to give 3-iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole (920 mg, 99% yield) as a pale 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).
