1: 3-ethenyl-1-phenylsulfonyl-1H-indole With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 1 h; 2: N,N-dimethyl acetamide in tetrahydrofuran T=-78 - -10°C; 3: With hydroxylamine hydrochloride; sodium acetate in 1,2-dichloro-benzene 8 h; Heating;

1: LDA / tetrahydrofuran 2: NH2OH*HCl; AcONa / 1,2-dichloro-benzene / Heating View Scheme

1: 3-ethenyl-1-phenylsulfonyl-1H-indole With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 1 h; 2: benzonitrile in tetrahydrofuran T=-78 - -10°C; 3: With hydroxylamine hydrochloride; sodium acetate in 1,2-dichloro-benzene 8 h; Heating;

1: 77 percent / LDA / hexane; tetrahydrofuran / 1.) -78 to 0 deg C, 45 min; 25 deg C, 3 h, 2.) -78 deg C, 5 min; -78 to 0 deg C 2: 98 percent / Br2 / CH2Cl2; CCl4 / 3 h / 25 °C 3: 99 percent / NaH / tetrahydrofuran; paraffin / 1.) 0 deg C, 10 min; 0 to 25 deg C, 10 min, 2.) reflux, 2 h 4: 85 percent / p-TsOH, molecular sieves 4 Angstroem / toluene / 4 h / Heating 5: 48 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 10 min, 2.) reflux, 3 h View Scheme

potassium hydroxide; 18-crown-6 ether 1) MeCN, 1h, 85 deg C 2) 1h, 85 deg C; Yield given. Multistep reaction;

1: 23 percent / LDA/n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2: 38 percent / hydroxylamine/NaOAc / toluene / 48 h / Heating View Scheme

1: 3-ethenyl-1-phenylsulfonyl-1H-indole With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 1 h; 2: furan-2-carbonitrile in tetrahydrofuran T=-78 - -10°C; 3: With hydroxylamine hydrochloride; sodium acetate in 1,2-dichloro-benzene 8 h; Heating;