I[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[NH:5][CH:6]=1.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[CH:17])[CH:11]=1.C(N(CC)CC)C.CCCCCC>CN(C=O)C.O.[Cu](I)I.C(OCC)(=O)C>[Br:9][C:10]1[CH:11]=[C:12]([C:16]#[C:17][C:2]2[CH:3]=[C:4]([CH:7]=[O:8])[NH:5][CH:6]=2)[CH:13]=[CH:14][CH:15]=1
A solution of 4-iodo-1H-pyrrole-2-carbaldehyde (0.50 g; 2.262 mmol) and bis(triphenylphosphine)palladium-(II)chloride (0.079 g; 0.113 mmol)) in DMF (15 mL; degassed with nitrogen for 30 minutes) was stirred at ambient temperature for 15 minutes. Then the following were added: 1-bromo-3-ethynylbenzene (0.61 g; 3.394 mmol), copper iodide (43 mg; 0.226), and triethylamine (1.58 mL, 11.3 mmol). The course of the reaction was followed with TLC (4:1, hexane:ethyl acetate). After 2 hours the reaction mixture was diluted with water and the organic material was extracted into dichloromethane. The organic extracts were washed with water and brine, dried over MgSO4, filtered, and evaporated. The residue was chromatographed on silica gel using 3:1 hexane:ethyl acetate to yield 0.58 g (93%) of the title compound as a yellow crystalline solid, mp 152-156° C.; MS (ES) m/z 272.0, [M−H]−.
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