反应详情

5-[4-(Pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-amine hydrobromide salt (167.5 mg, 0.5 mmol) was suspended in 2 mL of anhydrous pyridine. Neat 2,2-difluoro-1,3-benzodioxole-5-carbonyl chloride (165.4 mg, 0.75 mmol) was added directly into the solution. The reaction mixture formed an orange-red solution with a small amount of white precipitate. It was left to stir for 3 hours. Then it was diluted with ca. 1 mL of MeOH, filtered through 0.22 u syringe filter and purified by reverse phase preparative HPLC using acetonitrile/water mixture containing 0.01% of TFA. Fractions, containing the product, were combined and partitioned between ca. 40 mL of EtOAc and ca. 40 mL of saturated aqueous NaHCO3. The EtOAc layer was washed with brine, dried over anhydrous sodium sulfate and filtered. Solvent was removed in vacuo to give the title product as a yellow solid (27.0 mg). Yield 12.3%.

1. customThe reaction mixture formed an orange-red solution with a small amount of white precipitate
2. waitIt was left
3. filtrationfiltered through 0.22 u syringe
4. filtrationfilter
5. custompurified by reverse phase preparative HPLC
6. additioncontaining 0.01% of TFA
7. additionFractions, containing the product
8. custompartitioned between ca. 40 mL of EtOAc and ca. 40 mL of saturated aqueous NaHCO3
9. washThe EtOAc layer was washed with brine
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationfiltered
12. customSolvent was removed in vacuo