Sodium Carbonate → HCID 18363874, compound

Participants

Reaction Steps

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (45 mg, 0.134 mmol) (Starting Material 1), 2M aqueous Na2CO3 solution (134 μL , 0.268 mmol), (Ph3P)4Pd (5 mg, 0.004 mmol) (Aldrich), and 4-hydroxyphenylboronic acid (37 mg, 0.268 mmol) (prepared according to H. Gilman et al., J. Am. Chem. Soc. 79:3077-3081 (1957)) in 3 mL of a 3:1 mixture of 1,2-dimethoxyethane:distilled water was heated at reflux under a nitrogen atmosphere for 15 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, 35% ethyl acetate-hexanes elution) to yield pure (Z)-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (yield: 32 mg, 79%) as a yellow solid (mp 271-273° C.).

Provenance & Evidence