1.1: palladium diacetate; potassium iodide; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; triethylamine / ethyl acetate / 16 h / 50 °C / |Inert atmosphere; |Schlenk technique 2.1: methanol / ethyl acetate / 1 h / -5 - 20 °C / |Inert atmosphere; |Schlenk technique 2.2: 4 h / 20 °C / |Inert atmosphere; |Schlenk technique View Scheme

1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 0.5 h / 200 °C / microwave irradiation 2: 48 percent / tetrahydrofuran / 0.08 h / 1 °C View Scheme

1: 5-chloro-1H-indole With tri[2-(2-methoxyethoxy)ethyl]amine; potassium tert-butylate in benzene T=20°C; 24 h; 2: methyl iodide in benzene T=20°C; 1 h;

1: 5-chloro-1H-indole With sodium hydride in N,N-dimethyl-formamide T=20°C; 4 h; 2: methyl iodide in N,N-dimethyl-formamide T=20°C; 15 h;

in (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide

potassium hydroxide in N,N-dimethyl-formamide; methyl iodide

1,8-diazabicyclo[5.4.0]undec-7-ene in sulfolane T=240°C; 0.333333 h;

1: 1.) SnCl4, Bu3N, 2.) KOH, H2O / 1.) chlorobenzene, -50 deg C to 80 deg C, 2.) chlorobenzene, THF, reflux 2: 83 percent / quinone, LiCl / PdCl2(MeCN)2 / tetrahydrofuran / 18 h / Heating View Scheme

in benzene 0.5 h; Heating;

1: sodium cyanoborohydride; acetic acid / water; acetonitrile / 6 h / 20 °C 2: triethyl borane; oxygen; N-ethylpiperidinium hypophosphite / 1,4-dioxane; hexane / 2 h / 73 °C / Air atmosphere View Scheme