Potassium Carbonate → 3-((3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide

To a solution of 3-(2-(benzyloxy)-4-chlorophenyl)-5-(bromomethyl)-1,2,4-thiadiazole (0.33 g, 0.83 mmol) in DMF (10 ml) was added 2,6-difluoro-3-hydroxybenzamide (0.13 g, 0.75 mmol) and potassium carbonate (0.403 g, 2.92 mmol). The reaction mixture was stirred at room temperature for 16 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under vacuum, added 25 ml water and extracted with ethyl acetate (3×25 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 40% EtOAc-Hexane) to get the desired product (0.123 g, 30%).

1. customAfter the completion of the reaction (TLC monitoring)
2. customthe reaction mixture was evaporated to dryness under vacuum
3. additionadded 25 ml water
4. extractionextracted with ethyl acetate (3×25 ml)
5. dry with materialThe combined organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe crude residue was purified over silica gel (100-200 M, 40% EtOAc-Hexane)

ORD record

ord-b8b40631b5bc4c6095265de673faeb39

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492414B2