Dichloromethane → 1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(7-fluoroquinolin-6-yl)ethanol

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Reaction Steps

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(7-fluoro-quinolin-6-yl)-methanone (Stage 174.2, 294 mg, 0.9 mmol) was dissolved in anhydrous THF (70 mL) at 40° C. and methylmagnesium bromide in Et2O (3 M, 0.36 mL) was slowly added and the RM was then allowed to cool down to rt and stirred for 2 h. More methylmagnesium bromide in Et2O (3 M, 0.5 mL) was added and the RM was stirred for 1 h more. It was then taken into DCM and 10% aqueous NaHCO3 solution and extracted. The organic phase was dried on MgSO4. After evaporation of the solvent the crude was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, EtOAc/MeOH=100:0->90:10) to afford the title compound (tR 3.74 min (conditions 3), MH+=343, 1H-NMR in DMSO-d6: 8.87 (dd, 1H); 8.50 (d, 1H); 8.49 (d, 1H); 8.18 (d, 1H); 7.85 (s, 1H); 7.59 (d, 1H); 7.51 (dd, 1H); 7.23 (d, 1H); 6.33 (s, 1H); 2.13 (s, 3H))

Provenance & Evidence