Nitroethane → 6-fluoro-3-(2-nitropropenyl)-1H-indole

반응식

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[N+:13]([CH2:16][CH3:17])([O-:15])=[O:14].C([O-])(=O)C.[NH4+]>CCOC(C)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[C:16]([N+:13]([O-:15])=[O:14])[CH3:17])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

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실험 절차

6-Fluoro-3-(2-nitropropenyl)-1H-indole was prepared by combining 6-fluoroindole-3-carboxaldehyde (485 mg, 2.97 mmol), nitroethane (6.0 mL), and ammonium acetate (250 mg, 3.27 mmol). The reaction solution was allowed to reflux 2 hours. The reaction solution was diluted with EtOAc (100 mL), washed with H2O (50 mL×2), partitioned, dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 560 mg (86% yield) of 6-fluoro-3-(2-nitropropenyl)-1H-indole; 1H NMR (CDCl3) δ 11.03 (1H, br s), 8.41 (1H, s), 7.63 (1H, dd), 7.50 (1H, s), 7.06 (1H, dd), 6.92 (1H, t), 2.44 (3H, s); TLC (SiO2 plate, 100% DCM) Rf=0.7.