反应详情

温度

110 °C

Dibenzylideneacetone (1.1 mg) and 1,10-phenanthroline (17 mg) were mixed in dry toluene (1 mL) under argon for 5 minutes, followed by addition of copper(II) trifluoromethanesulfonate (1.8 mg), cesium carbonate (35 mg), pyrrole (10 mg) and N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide (1p, 30 mg) and the reaction was heated to 110° C. in a sealed 4 mL vial under argon for 48 hours. The reaction mixture was concentrated in vacuo, sodium hydroxide (2 M, 1.5 mL) was added and the product was extracted with isopropyl acetate (3×1.5 mL). The combined organic phases were dried over magnesium sulfate, concentrated in vacuo and redissolved in dimethyl sulfoxide (0.50 mL) of which 0.25 mL was subjected to preparative LC-MS purification to furnish 1.3 mg (9% yield) of the title compound as an oil. LC-MS-TOF (m/z) 297 (MH+); tR=3.11, (UV, ELSD) 97%, 99%.

1. concentrationThe reaction mixture was concentrated in vacuo, sodium hydroxide (2 M, 1.5 mL)
2. additionwas added
3. extractionthe product was extracted with isopropyl acetate (3×1.5 mL)
4. dry with materialThe combined organic phases were dried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. dissolutionredissolved in dimethyl sulfoxide (0.50 mL) of which 0.25 mL
7. customwas subjected to preparative LC-MS purification