[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[NH:4][N:3]=1.Cl.Cl[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[N:4]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[N:3]=1A mixture of 3-iodo-6-methyl-1H-indazole (516 mg, 2 mmol), 2-chloro-N,N-dimethylethanamine hydrochloride (346 mg, 2.4 mmol) and potassium carbonate (828 mg, 6 mmol) in 20 mL of DMF was heated to 80 degree overnight. After cooling to room temperature, water (50 mL) was added, product extracted with dichloromethane (3×50 mL), combined organics were dried with sodium sulfate, and concentrated to give 2-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylethanamine (1 g, 100%). 1H NMR (300 MHz, CDCl3): δ 7.33 (d, 1H, J=8.1 Hz), 7.15 (s, 1H), 7.03 (d, 1H, J=0.6 Hz), 4.47 (t, 2H, J=7.2 Hz), 2.81 (t, 2H, J=7.2 Hz), 2.51 (s, 3H), 2.34 (m, 6H).
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