反应详情

5-Bromo-4-methyl-1,3-thiazole (500 mg, 2.8 mmol) and CuI (120 mg, 0.63 mmol) were combined in DME (5 mL) and argon gas was bubbled through the suspension for several minutes to deoxygenate the mixture. Triethylamine (2.0 mL, 14 mmol) and PdCl2(PPh3)2 (220 mg, 0.32 mmol) were added, followed by the dropwise addition of (2-fluorophenyl)acetylene (1.0 g, 8.3 mmol). The reaction mixture was heated and after 3 h at reflux, allowed to cool, diluted with ethyl acetate (20 mL), and filtered through Celite™. The filter pad was washed thoroughly with ethyl acetate and the combined filtrates were washed with water (20 mL), brine (20 mL), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography on silica gel eluting with 95:5 hexane:ethyl acetate to afford 5-[(2-fluorophenyl)ethynyl]-4-methyl-1,3-thiazole (690 mg, 56% yield) as a red oil. 1H NMR (CDCl3, 300 MHz) δ 8.65 (s, 1H), 7.53–7.47 (m, 1H), 7.36–7.26 (m, 1H), 7.17–7.09 (m, 2H), 2.62 (s, 3H). MS (ESI) 217.3 (M+).

1. customargon gas was bubbled through the suspension for several minutes
2. customto deoxygenate the mixture
3. temperatureThe reaction mixture was heated and after 3 h
4. temperatureat reflux
5. temperatureto cool
6. filtrationfiltered through Celite™
7. washThe filter pad was washed thoroughly with ethyl acetate
8. washthe combined filtrates were washed with water (20 mL), brine (20 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationThe filtrate was concentrated in vacuo
12. customthe residue was purified by column chromatography on silica gel eluting with 95:5 hexane