Iodine → 6-Chloro-3-[1-(4,6-difluoro-1-methyl-1H-indazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazine

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Reaction Steps

A solution of 1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(4,6-difluoro-1-methyl-1H-indazol-5-yl)-ethanol (530 mg, 1.457 mmol), Iodine (925 mg, 3.64 mmol) and phosphinic acid (50%, 0.556 mL) in 20 mL of acetic acid was heated at 110° C. for 2 h. Solvent was evaporated and the residue was dissolved in water, neutralized with saturated NaHCO3 solution and extracted with DCM three times. Organic layers were combined and washed with brine, dried over Na2SO4. Solvent was then evaporated and the crude was purified by flash chromatography (hexane:EtOAc=1:2) to give the title compound as light yellow solid (320 mg, 63.2%). 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.03 (s, 1H), 8.0 (d, 1H), 7.8 (s, 1H), 7.23 (d, 1H), 7.19 (d, 1H), 5.1 (q, 1H), 4.0 (s, 3H), 1.92 (d, 3H). LCMS (method B): [MH]+=347.9, tR=2.69 min.

Provenance & Evidence