Sodium Carbonate → HCID 18363871, compound

Participants

Reaction Steps

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (30 mg, 0.089 mmol) (Starting Material 1), 2M aqueous Na2CO3 solution (151 μL, 0.303 mmol), (Ph3P)2PdCl2 (3 mg, 0.004 mmol) (Aldrich), and 4-carboxyphenylboronic acid (18 mg, 0.108 mmol) (Lancaster) in 4.5 mL of a 2:1 mixture of 1,2-dimethoxyethane:distilled water was heated at reflux under a nitrogen atmosphere for 20 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, 40% ethyl acetate-hexanes then 50% ethyl acetate-hexanes with 1% glacial acetic acid elution) to yield pure (Z)-4-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-benzoic acid (yield: 33 mg, 91%) as an orange solid (mp 315-317° C.).

Provenance & Evidence