Triethylamine → (Z)-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-(fluorosulfonyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)-4-(3-aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (30 mg, 0.100 mmol) (from Example 4 supra) and Et3N (14 μL, 0.100 mmol) in 5 mL of chloroform was cooled to −78° C. and then treated with 4-(fluorosulfonyl)benzoyl chloride (24 mg, 0.109 mmol) (Aldrich). The reaction mixture was stirred at −78° C. under a nitrogen atmosphere for 1 hr and then heated at reflux. The reaction mixture was allowed to cool to room temperature and then diluted with chloroform. The organic phase was then washed, in sequence, as follows: with a saturated aqueous sodium bicarbonate solution, with distilled water, with a 1N aqueous hydrochloric acid solution, and finally with a saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 30% ethyl acetate-hexanes elution) yielded pure (Z)-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-(fluorosulfonyl)benzamide (yield: 25.6 mg, 53%) as a yellow solid (mp: 148-151° C.).

Provenance & Evidence