Dimethylformamide → 3-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine

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Reaction Steps

A mixture of 3-iodo-6-methyl-1H-indazole (2.58 g, 10 mmol), 3-chloro-N,N-dimethylpropan-1-amine hydrochloride (2.37 g, 15 mmol) and potassium carbonate (4.14 g, 30 mmol) in 50 ml, of DMF was heated to 85° C. for 3 hours. After cooling to room temperature, 100 mL of water was added and the mixture was extracted with ethyl acetate (4×100 mL). Then the combined organic phases were added with 20 mL of 6N HCl, and the solution was extracted with dichloromethane (4×50 mL). The combined organic phases were dried with sodium sulfate, concentrated to give 3-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine (1.74 g, 50.6%). LCMS: (M+H)+=344; 1H NMR (300 MHz, CDCl3): δ 7.33 (d, 1H, J=8.4 Hz), 7.21 (s, 1H), 7.03 (d, 1H, J=8.4 Hz), 4.43 (t, 2H, J=6.6 Hz), 2.51 (s, 3H), 2.27-2.23 (m, 8H), 2.09-2.07 (m, 2H).

Provenance & Evidence