Thionyl bromide → Methyl 5-bromo-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate

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Reaction Conditions

Reaction Steps

Methyl 4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate (690 mg, 2.66 mmol) was dissolved in thionyl bromide (5 mL, 64.5 mmol) and heated at 50° C. in a sealed tube for 4 h. The solution poured over ice and quenched with ammonium hydroxide. The aqueous layer was extracted with dichloromethane (×3). The organic layers put together, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford the title compound as a light brown solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.66 (d, 1H); 8.27 (s, 1H); 8.25 (s, 1H); 8.25 (d, 1H); 7.35 (dd, 1H); 3.85 (s, 3H). LRMS (APCI) calc'd for (C12H8BrN3O2S) [M+H]+, 338.0. found 337.9.

Provenance & Evidence