N-(3-iodophenyl)acetamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In analogy to Example 13ap), from N-benzyl-5-bromo-isatin (G.Tacconi et al., J. Prakt. Chem. 315, 339 (1973)) there is obtained the corresponding N-benzyl-5-bromo-isatin oxime as a yellow solid. Yield: 94%. Mass spectrum: peaks inter alia at 330 (M+, 17%); 285 (14%), 91 (100%). 13ar) 1.36 g of N-acetyl-3-iodo-aniline are dissolved in 25 ml of methylene chloride and treated with 61 mg of 4-dimethylamino-pyridine. A solution of 5.25 ml of cyclopropanecarbonyl chloride in 7 ml of methylene chloride is added dropwise to this solution. The mixture is stirred at room temperature overnight, then poured into 100 ml of water and made weakly acid with a few drops of dil. hydrochloric acid. Extraction with ethyl acetate and chromatography on silica gel with ethyl acetate gives 1.85 g of cyclopropanecarboxylic acid acetyl-(3-iodo-phenyl)-amide as a yellowish oil which solidifies in time. Yield: 92%. Mass spectrum: peaks inter alia at 329 (M+, 8%); 287 (58%), 69 (100%). Extraction with ethyl acetate and chromatography on silica gel with ethyl acetate

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the compound from Example 3 (E1) (0.2 g, 0.64 mmol) and 3-acetamido-1-iodobenzene (0.17 g, 0.64 mmol) in triethylamine (5 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palladium(0), copper(I) iodide and triphenylphosphine. The mixture was heated at 80° C. for 0.3 h, was cooled to room temperature and was concentrated in vacuo. The residue was purified by flash chromatography, eluting with 1:1 hexanes/ethyl acetate, to provide the title compound as tan solid (0.17 g, 60%), m.p. 58°-60° C. was cooled to room temperature was concentrated in vacuo The residue was purified by flash chromatography eluting with 1:1 hexanes/ethyl acetate

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the compound from Example 3 (E1) (0.2 g, 0.64 mmol) and 3-acetamido-1-iodobenzene (0.17 g, 0.64 mmol) in triethylamine (5 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palladium(0), copper(I) iodide and triphenylphosphine. The mixture was heated at 80° C. for 0.3 h, was cooled to room temperature and was concentrated in vacuo. The residue was purified by flash chromatography, eluting with 1:1 hexanes/ethyl acetate, to provide the title compound as tan solid (0.17 g, 60%), m.p. 58-60° C. was cooled to room temperature was concentrated in vacuo The residue was purified by flash chromatography eluting with 1:1 hexanes/ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In analogy to Example 13ap), from N-benzyl-5-bromo-isatin (G.Tacconi et al., J. Prakt. Chem. 315, 339 (1973)) there is obtained the corresponding N-benzyl-5-bromo-isatin oxime as a yellow solid. Yield: 94%. Mass spectrum: peaks inter alia at 330 (M+, 17%); 285 (14%), 91 (100%). 13ar) 1.36 g of N-acetyl-3-iodo-aniline are dissolved in 25 ml of methylene chloride and treated with 61 mg of 4-dimethylamino-pyridine. A solution of 5.25 ml of cyclopropanecarbonyl chloride in 7 ml of methylene chloride is added dropwise to this solution. The mixture is stirred at room temperature overnight, then poured into 100 ml of water and made weakly acid with a few drops of dil. hydrochloric acid. Extraction with ethyl acetate and chromatography on silica gel with ethyl acetate gives 1.85 g of cyclopropanecarboxylic acid acetyl-(3-iodo-phenyl)-amide as a yellowish oil which solidifies in time. Yield: 92%. Mass spectrum: peaks inter alia at 329 (M+, 8%); 287 (58%), 69 (100%). Extraction with ethyl acetate and chromatography on silica gel with ethyl acetate

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the compound from Example 3 (E1) (0.2 g, 0.64 mmol) and 3-acetamido-1-iodobenzene (0.17 g, 0.64 mmol) in triethylamine (5 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palladium(0), copper(I) iodide and triphenylphosphine. The mixture was heated at 80° C. for 0.3 h, was cooled to room temperature and was concentrated in vacuo. The residue was purified by flash chromatography, eluting with 1:1 hexanes/ethyl acetate, to provide the title compound as tan solid (0.17 g, 60%), m.p. 58°-60° C. was cooled to room temperature was concentrated in vacuo The residue was purified by flash chromatography eluting with 1:1 hexanes/ethyl acetate