反应详情

温度

130 °C

To a solution of 2-bromo-5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazole (D4) (100 mg), 2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (D5) (85 mg) and tripotassium phosphate (145 mg) in N,N-dimethylformamide (DMF) (6 mL) and water (1.5 mL) stirred under nitrogen at room temperature was added Pd(Ph3P)4 (31.5 mg). The reaction vessel was sealed and heated under microwave at 130° C. for 8 min. After cooling the reaction, water was added to quench the reaction. After filtered through the celite, the filtrate was partitioned between the organic and aqueous layers. The aqueous layer was extracted with EA for 3 times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate. The dried solution was concentrated, and purified by column chromatography to afford 2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}benzaldehyde (D6) (60.4 mg). MS (ES): C21H19F3N2O2S requires 420. found 421.1 (M+H+).

1. customThe reaction vessel was sealed
2. temperatureAfter cooling
3. additionwas added
4. customto quench
5. customthe reaction
6. filtrationAfter filtered through the celite
7. customthe filtrate was partitioned between the organic and aqueous layers
8. extractionThe aqueous layer was extracted with EA for 3 times
9. washThe combined organic layers were washed with brine
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationThe dried solution was concentrated
12. custompurified by column chromatography