3-Nitrophenylboronic Acid → HCID 15552084, compound

Participants

Reaction Steps

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (35 mg, 0.104 mmol) (Starting Material 1), Et3N (58 μL, 0.415 mmol), tri-o-tolylphosphine (6 mg, 0.020 mmol) (Aldrich), Pd(OAc)2 (2 mg, 0.009 mmol) (Aldrich), and 3-nitrophenylboronic acid (26 mg, 0.156 mmol) (Aldrich) in 3 mL of dry N,N-dimethylformamide was heated at 100° C. for 16 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-(3-nitrophenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (24.1 mg, 70%) as an orange solid (mp 197-199° C.).

Provenance & Evidence