反应详情

温度

70 °C

5-Bromo-2-methyl-thiazole-4-carbonitrile (4.8 g, 23.6 mmol) was suspended in 50 ml triethyl amine. Trimethylsilylacetylene (4.64 g, 47.3 mmol), triphenylphosphine (186 mg, 0.7 mmol) and bis(triphenylphosphine)palladium(II)chloride (0.83 g, 1.18 mmol) were added and this mixture was evacuated and purged with argon several times to remove oxygen from the solution. Copper(I)iodide (45 mg, 0.24 mmol) was added and the reaction mixture was stirred at 70° C. for 5 hrs. The residue was taken up in water, extracted three times with ethyl acetate and several times with water. The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by chromatography on silica gel (heptane/ethyl acetate 90:10->1:1 gradient). The desired product was obtained as a black solid (4.1 g, 79%).

1. customthis mixture was evacuated
2. custompurged with argon several times
3. customto remove oxygen from the solution
4. extractionextracted three times with ethyl acetate and several times with water
5. dry with materialThe combined organic extracts were dried with sodium sulfate
6. filtrationfiltered
7. customevaporated
8. customThe crude product was purified by chromatography on silica gel (heptane/ethyl acetate 90:10->1:1 gradient)