sodium hydroxide; tetrabutylammomium bromide in dichloromethane T=20°C; 1 h;

1,8-diazabicyclo[5.4.0]undec-7-ene T=59.84°C; 3 h;

in tetrahydrofuran T=25°C; 0.25 h;

1: 1,1'-carbonyldiimidazole; phenol With 4-(N,N-dimethlyamino)pyridine in acetonitrile Substitution; 2: indole in acetonitrile Acylation; Heating;

1: carbonic acid diphenyl ester With polystyrene-supported 1,8-diazabicyclo[5.4.0]-undec-7-ene in neat (no solvent) T=119.84°C; 2 h; Inert atmosphere; 2: indole in neat (no solvent) T=119.84°C; 3 h; Inert atmosphere; TimeTemperature;

1: 1.) n-BuLi / 1.) diethyl ether, 0 deg C, 30 min, 2.) diethyl ether, 25 deg C, 2 h 2: 86 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDCI*HCl) / CH2Cl2 / 0.25 h / 25 °C 3: 93 percent / tetrahydrofuran / 0.25 h / 25 °C View Scheme

1: 86 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDCI*HCl) / CH2Cl2 / 0.25 h / 25 °C 2: 93 percent / tetrahydrofuran / 0.25 h / 25 °C View Scheme