Triethylamine → (Z)-1,3-dihydro-4-phenyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Participants

Reaction Steps

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (30.4 mg, 0.090 mmol) (Starting Material 1), Et3N (38 μL, 0.271 mmol), tri-o-tolylphosphine (1.7 mg, 0.006 mmol) (Aldrich), Pd(OAc)2 (0.6 mg, 0.003 mmol)(Aldrich), and phenylboronic acid (16.5 mg, 0.136 mmol) (Aldrich) in 362 μL of dry N,N-dimethylformamide (Fisher Scientific) was heated at 100° C. for 24 h. The reaction mixture was allowed to cool to room temperature, concentrated in vacuo to remove N,N-dimethylformamide, and then directly purified by flash chromatography (Merck Silica gel 60, 70-230 mesh, 10% ethyl acetate-hexanes then 25% ethyl acetate-hexanes elution) to provide pure (Z)-1,3-dihydro-4-phenyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Yield 21.9 mg, 85%) as an orange solid (mp 184-185° C.).

Provenance & Evidence