反应详情

A vial was charged with (S)-2′-amino-3-(tetrahydro-2H-pyran-4-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (70.0 mg, 0.144 mmol), 5-chloro-2-fluorophenylboronic acid (75 mg, 0.433 mmol), potassium carbonate (100 mg, 0.721 mmol), and Pd(PPh3)4 (8.33 mg, 7.21 μmol). The vial was flushed with Ar (g), then Dioxane (721 μL) and water (0.3 mL) were added in sequence. The vial was sealed and placed in an 80° C. for 1.5 hours. The mixture was diluted with brine (20 mL) and extracted with EtOAc (2×15 mL). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was chromatographed on a 24-g Redi-Sep Gold column with 0-60% of a 90:10:1 mix of DCM/MeOH/NH4OH in DCM to give (S)-7-(5-chloro-2-fluorophenyl)-3-(tetrahydro-2H-pyran-4-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine.

1. customThe vial was flushed with Ar (g)
2. additionDioxane (721 μL) and water (0.3 mL) were added in sequence
3. customThe vial was sealed
4. additionThe mixture was diluted with brine (20 mL)
5. extractionextracted with EtOAc (2×15 mL)
6. dry with materialThe combined organic extracts were dried over sodium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe residue was chromatographed on a 24-g Redi-Sep Gold column with 0-60% of a 90:10:1
10. additionmix of DCM/MeOH/NH4OH in DCM