1-(6-Chloroimidazo(1,2-b)pyridazin-3-yl)ethan-1-one → 1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(4,6-difluoro-1-methyl-1H-indazol-5-yl)-ethanol

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Reaction Steps

N-BuLi, 6.88 mL, was added dropwise to a solution of 4,6-difluoro-1-methyl-1H-indazole ((xvi), 1.68 g, 10 mmol) in dry THF (50 mL) at −78° C. The solution was stirred at this temperature for 1 h, and then the solution of 1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)ethanone (CAS 90734-71-7, 1.95 g, 10 mmol) in 50 mL THF was added dropwise at −70/75° C. After stirring additional 3 h at −70/75° C. the RM was quenched with NH4C110%, and at 0° C. diluted with water, and extracted with EtOAc (3×). The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography to afford the title compound as a yellow foam (tR 4.40 min (conditions 5), MH+=364.2, 1H-NMR in DMSO-d6: 8.16 (d, 1H); 8.11 (s, 1H); 7.85 (s, 1H); 7.30 (d, 1H); 7.22 (d, 1H); 6.26 (s, 1H); 3.96 (s, 3H); 2.12 (d, 3H)).

Provenance & Evidence