Benzene → HCID 15552086, compound

Participants

Reaction Steps

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (70 mg, 0.208 mmol) (Starting Material 1), 2M aqueous Na2CO3 solution (210 μL, 0.420 mmol), (Ph3P)4Pd (10 mg, 0.009 mmol) (Aldrich), and 2,4-dichlorophenylboronic acid (44 mg, 0.231 mmol) (Lancaster) in 6 mL of a 5:1 mixture of benzene:1,2-dimethoxyethane was heated at reflux under a nitrogen atmosphere for 18 h. The reaction mixture was allowed to cool to room temperature and then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60% ethyl acetate-hexanes elution) to yield pure (Z)-4-(2,4-dichlorophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (yield 52 mg, 69%) as a yellow-brown solid (mp 185-187° C.).

Provenance & Evidence