Sodium hydride → 3-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one

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Reaction Steps

(3,4-Dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone (100 mg, 0.4 mmol), oxindole (100 mg, 0.8 mmol), pyrrolidine (0.2 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (a few drops) in dimethylforamide (1.5 mL) was heated at 160° C. for 2 hours. Sodium hydride (18 mg) was added to the reaction mixture and the heating was continued at 160° C. for 3 days. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was chromatographed eluting with ethyl acetate and hexane to give 5 mg of 3-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one. MS EI 374 [M]+.

Provenance & Evidence