[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=1.[H-].[Na+].C1O[CH2:30][CH2:29]OCCOCCOCCOC1.[S:32](Cl)(Cl)(=[O:34])=[O:33]>O1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:32]([C:30]2[CH:29]=[CH:3][CH:8]=[CH:9][C:10]=2[C:11]#[N:12])(=[O:34])=[O:33])[CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=1
To a solution (28 mL) of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (284 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 181 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (992 mg) was added dropwise and the mixture was stirred for 30 min, (2-cyanobenzene) sulfonyl chloride (606 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3) to give the title compound as colorless crystals (yield 410 mg, 77%).
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