4-Methoxystyrene → 1,3-dihydro-4-[(E)-2-(4-methoxyphenyl)-ethenyl]-(Z)-3-[(1H-pyrrol-2-yl)methlene]-2H-indol-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (from Example 71 above) (100 mg, 0.29 mmol) in DMF (3 mL) and TEA (2 mL) was added p-methoxy-styrene (79 mg, 0.58 mmol) (from Step A above), tri-o-tolylphosphine (107 mg, 0.35 mmol) (Aldrich) and Pd(OAc)2 (20 mg, 0.089 mmol) (Aldrich). The reaction mixture was stirred at 85° C. overnight in a pressure tube. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (Hex:EtOAc=5:1) to provide 1,3-dihydro-4-[(E)-2-(4-methoxyphenyl)-ethenyl]-(Z)-3-[(1H-pyrrol-2-yl)methlene]-2H-indol-2-one as a yellow solid. (Yield 72 mg, 73%).

Provenance & Evidence