water; sodium hydroxide in ethanol 8 h; Reflux;

1: 1-(phenylsulfonyl)-1H-indole With lithium diisopropyl amide in tetrahydrofuran T=-78 - 20°C; Inert atmosphere; 2: ethyl iodide in tetrahydrofuran T=-78 - 20°C; Inert atmosphere;

aluminium trichloride; tert-butylamine borane in dichloromethane

1: 1.) lithium diisopropylamide / 1.) hexane, THF, -70 deg C, 1.5 h, 2.) from -75 deg C to RT, overnight 2: 86 percent / aluminum chloride / CH2Cl2 / 1 h 3: 71 percent / AlCl3, borane-tert-butylamine complex / CH2Cl2 View Scheme

1: 86 percent / aluminum chloride / CH2Cl2 / 1 h 2: 71 percent / AlCl3, borane-tert-butylamine complex / CH2Cl2 View Scheme