反应详情

温度

0 °C

3-Bromo-7-iodo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine (500 g, 1.055 mmol) and potassium carbonate (0.729 g, 5.27 mmol) were dissolved in DMF (7.03 mL) and stirred for 5 min. The reaction was cooled to 0° C. and SEM-Cl (0.561 mL, 3.16 mmol) was added slowly dropwise. The reaction was warmed to RT and stirred overnight. The mixture was poured into a separatory funnel containing water (25 mL) and EtOAc (15 mL). The aqueous layer was extracted with EtOAc (3×20 mL), and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (0-50% EtOAc:Hex) to afford 3-bromo-7-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine, isolated as a pink solid.

1. temperatureThe reaction was warmed to RT
2. stirringstirred overnight
3. additionThe mixture was poured into a separatory funnel
4. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
5. washthe combined organic layers were washed with brine
6. dry with materialdried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe material was purified via column chromatography (0-50% EtOAc:Hex)