Sodium Carbonate → HCID 59971438, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (50 mg, 0.149 mmol) (Starting Material 1), 2M aqueous Na2CO3 solution (149 μL , 0.298 mmol), (Ph3P)4Pd (5 mg, 0.004 mmol) (Aldrich), and 2-methoxyphenylboronic acid (25 mg, 0.164 mmol) (Aldrich) in 4 mL of a 2:1 mixture of 1,2-dimethoxyethane:distilled water was heated at 100° C. 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, 20% ethyl acetate-hexanes elution) to provide a crude yellow solid. Recrystallization from chloroform-pentane yielded pure (Z)-1,3-dihydro-4-(2-methoxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Yield 37 mg, 79%) as yellow crystals (mp 223-225° C.).

Provenance & Evidence