Iodobenzoic ethyl ester

To a 0.9 mL THF solution containing 4.3 mg Pd(OAc)2 (0.02 mmol, 10 mol %), tri-2-furylphosphine (5.1 mg, 0.02 mmol, 10 mol %), 32.7 mg triethylamine (0.32 mmol), and 75.2 mg 4-iodobenzoic acid ethyl ester (0.27 mmol), was added 65.7 mg (2-pyridyl)-l-hexenyl-dimethylsilane (0.30 mmol) under argon the reaction mixture was stirred at 60°C for 3 h. After the mixture was cooled to room temperature, 48.2 mg 4-iodoacetophenone (0.20 mmol) and 0.46 mL 1 M TBAF solution in THF were added to the reaction mixture, and this reaction mixture was stirred at 60°C for 14 h. The catalyst was removed by filtration through a short silica gel pad (EtOAc). The filtrate was evaporated, and the residue was chromatographed on silica gel (hexane/EtOAc, 10/1) to afford 48.6 mg ( )-l-(4-acetyl)phenyl-2-(4-ethoxycarbonyl)phenyl-l-hexene as a colorless oil, in a yield of71%. 

The design of a novel series of cycUn-dependent kinase (CDK) inhibitors with a macrocyclic quinoxaline-2-one 208 is reported (Kawanishi et al. 2006), where 208 was synthesized as shown in Scheme 5.50. The deprotonation of the fluorine-adjacent position of l-fluoro-2-iodobenzene 209, with LDA, followed by the carbon dioxide trapping and then esterification of the carboxylic acid, led to methyl 2-fluoro-3-iodobenzoate. The iodomagnesium exchange of methyl 2-fluoro-3-iodobenzoate according to Knochel s procedure (Knochel et al. 2003) followed by chloroglyoxylic acid ethyl ester resulted in ketoester 210, which was coupled with 3-[(tert-bulyldimethylsilyl)oxy]benzene-1,2-diamine to... 

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