Iodine → 6-(1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)ethyl)-7-fluoroquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of (rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(7-fluoro-quinolin-6-yl)ethanol (Stage 174.1, 200 mg, 0.584 mmol) in acetic acid (3.2 mL) were added iodine (296 mg, 1.167 mmol) and H3PO2 (0.642 mL of a 50% aqueous solution, 5.84 mmol). The RM was heated at 150° C. for 30 min. After cooling down to rt the acetic acid was evaporated under reduced pressure, water was added and the solution was neutralized with a solution of 10% NaHCO3. The product which precipitated was extracted with DCM, the combined organic phase were dried over MgSO4, filtered, evaporated to dryness and the residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, hexane/EtOAc=50:50->0:100) to afford the title compound as a off white crystalline solid (tR 4.61 min (conditions 3), MH+=327.2, 1H-NMR in DMSO-d6: 8.85 (dd, 1H); 8.28 (dd, 1H); 8.20 (d, 1H); 7.85 (s, 1H); 7.78-7.68 (2H, m); 7.44 (dd, 1H); 7.29 (d, 1H); 4.95 (q, 1H); 1.79 (d, 3H)).

Provenance & Evidence