Reaktion #167783

Reaktionsgleichung

3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

trimethylsilylacetylene

Et3N

→

3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl) phenyl)benzamide

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a pressure tube with one end sealed
2. 2
   TemperaturAfter cooling to room temperature
3. 3
   Filtrationthe solution was filtered by 2 cm silica gel column
4. 4
   FiltrationThe filtration
5. 5
   Waschenis washed three times with ethyl acetate
6. 6
   Einengenis concentrated to brown solid which
7. 7
   workup.DISSOLUTIONis further dissolved in 5 mL methanol
8. 8
   workup.ADDITIONThe solution is then added with 980 mg K2CO3
9. 9
   workup.STIRRINGstirred at room temperature for 3 h
10. 10
    FiltrationThe solid was filtered off
11. 11
    Einengenthe solution was concentrated to column chromatography f 344 mg desired product

Vorschrift

In a pressure tube with one end sealed, add 485 mg 3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (1.0 mmol) from Step 2, 500 mg trimethylsilylacetylene (5.0 mmol), 19 mg Cu I (0.1 mmol), 7 mg Pd(PPh3)2Cl2 (0.01 mmol), 1.0 mL Et3N in 3.0 mL acetonitrile, and after Nitrogen replacement, the mixture is stirred at 80° C. for 2 h. After cooling to room temperature, the solution was filtered by 2 cm silica gel column. The filtration is washed three times with ethyl acetate and is concentrated to brown solid which is further dissolved in 5 mL methanol. The solution is then added with 980 mg K2CO3 and stirred at room temperature for 3 h. The solid was filtered off and the solution was concentrated to column chromatography f 344 mg desired product. (90%)

Quelle