反应详情

温度

100 °C

Methyl-5-bromo-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate (200 mg, 0.591 mmol), potassium vinyltrifluoroborate (119 mg, 0.887 mmol), PdCl2(dppf)-CH2Cl2 adduct (48 mg, 0.059 mmol), and triethylamine (0.165 mL, 1.18 mmol) was dissolved in n-propanol (5.91 mL) and purged with nitrogen for 5 minutes in a sealed tube. The solution was heated at 100° C. for 18 h. the reaction was cooled to room temperature and quenched with saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (×3) and the organic layers combined, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford the title compound as an orange solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.61 (d, 1H); 8.23 (d, 1H); 8.16 (s, 1H); 7.95 (s, 1H); 7.32 (dd, 1H); 6.94 (dd, 1H); 5.87 (d, 1H); 5.44 (d, 1H); 3.85 (s, 3H). LRMS (APCI) calc'd for (C14H11N3O2S) [M+11]+, 286.1. found 286.0.

1. custompurged with nitrogen for 5 minutes in a sealed tube
2. temperaturewas cooled to room temperature
3. customquenched with saturated sodium bicarbonate
4. extractionThe aqueous layer was extracted with ethyl acetate (×3)
5. dry with materialdried with magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by flash chromatography