1,10-Phenanthroline → 2-Cyclopentyl-N-(2,6-dimethyl-4-pyrrol-1-yl-phenyl)-acetamide

Participants

Reaction Conditions

Reaction Steps

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%.

Provenance & Evidence