Iodoethane → 6-{6-[1-(1-Ethyl-piperidin-4-yl)-1H-pyrazol-4-yl]-imidazo[1,2-b]pyridazin-3-ylmethyl}-7-fluoro-quinoline

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Reaction Steps

A mixture of 7-fluoro-6-[6-(1-piperidin-4-yl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline (Example 180, 50 mg, 0.117 mmol) and ethyliodide (19 μL, 0.234 mmol) in dioxane (1 mL) was stirred at rt for 2 h. Cs2CO3 (19 mg, 0.059 mmol) was then added and the RM was stirred at rt for 5 h more. The mixture was diluted with EtOAc and washed with NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with a 4 g RediSep® silica gel column, DCM/(DCM/MeOH 9:1+NH3)=100:0→0:100) to afford the title compound as a foam (tR 3.10 min (conditions 3), MH+=456.2, 1H-NMR in DMSO-d6: 8.84 (m, 1H); 8.50 (s, 1H); 8.34 (m, 1H); 8.08 (m, 2H); 8.04 (d, 1H); 7.76 (d, 1H); 7.60 (s, 1H); 7.53 (d, 1H); 7.47 (dd, 1H); 4.55 (s, 2H); 4.18 (m, 1H); 2.96 (m, 2H); 2.35 (q, 2H); 1.97 (m, 6H); 1.01 (t, 3H)).

Provenance & Evidence