反应详情

A vial was charged with (S)-2′-amino-3-bromo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol (380 mg, 1.091 mmol), potassium carbonate (754 mg, 5.46 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (688 mg, 3.27 mmol), pd(ph3p)4 (126 mg, 0.109 mmol), DMF (5457 μL), and water (2.5 mL). The vial was sealed, placed in 80° C. and heated overnight. The mixture was diluted with water (35 mL) and extracted with EtOAc (3×15 mL). The combined organic extract was dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on a 80-g Redi-Sep column, eluting with 0-100% of a 90:10:1 mix of DCM/MeOH/NH4OH in DCM to give (S)-2′-amino-3-(3,6-dihydro-2H-pyran-4-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol as an orange solid.

1. customThe vial was sealed
2. customplaced in 80° C.
3. temperatureheated overnight
4. extractionextracted with EtOAc (3×15 mL)
5. extractionThe combined organic extract
6. dry with materialwas dried over sodium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by chromatography on a 80-g Redi-Sep column
10. washeluting with 0-100% of a 90:10:1
11. additionmix of DCM/MeOH/NH4OH in DCM