1,2-Dimethoxyethane → HCID 59971439, 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 (30 mg, 0.089 mmol) (Starting Material 1) 2M aqueous Na2CO3 solution (89 μL, 0.178 mmol), (Ph3P)4Pd (5 mg, 0.004 mmol) (Aldrich), and 4-methylphenylboronic acid (15 mg, 0.110 mmol) (Aldrich) in 3 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, 25% ethyl acetate-hexanes elution) to provide a crude yellow solid containing product. The solid was dissolved in chloroform and precipitation by the addition of hexanes provided pure (Z)-1,3-dihydro-4-(4-methylphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (yield 19 mg, 71%) as a yellow solid (mp 217-218° C.).

Provenance & Evidence