hydrogenchloride; lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene addn. of boron compd. to a soln. of indole deriv. in THF, cooling to 0°C, dropwise addn. of Li salt in THF/heptane/ethylbenzene over 1 h,stirring for 30 min, addn. of 2 M HCl, stirring at room temp. for 10 mi n; sepn., extn. aq. layer with ethyl acetate, drying org layer with Na2SO4,filtration, evapn. in vac.;

n-butyllithium in tetrahydrofuran; hexane

1.1: 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 1 h / 20 °C 2.1: triisopropyl borate; LDA / tetrahydrofuran / 2 h / 0 °C 2.2: 97 percent / aq. phosphate buffer / tetrahydrofuran / pH 6.0 View Scheme

1.1: 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 1 h / 20 °C 2.1: triisopropyl borate; LDA / tetrahydrofuran / 2 h / 0 °C 2.2: 97 percent / aq. phosphate buffer / tetrahydrofuran / pH 6.0 View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethylene glycol dimethyl ether; water / 12 h / Inert atmosphere; Reflux 2.1: lithium hydroxide hydrate / tetrahydrofuran; water / 12 h / 60 °C 2.2: 20 °C 3.1: diphenyl phosphoryl azide; triethylamine / toluene / 1.5 h / 100 °C / Inert atmosphere; Microwave irradiation 4.1: 1,2-dichloro-benzene / 0.25 h / 180 °C / Inert atmosphere View Scheme

1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethylene glycol dimethyl ether; water / 12 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere 3: lithium hydroxide hydrate / tetrahydrofuran; water / 12 h / 60 °C 4: diphenyl phosphoryl azide; triethylamine / benzene / 1.5 h / 50 °C / Inert atmosphere 5: 1,2-dichloro-benzene / 0.25 h / 180 °C / Inert atmosphere View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; water; toluene T=100°C; Suzuki-Miyaura cross-coupling; 3 h; Inert atmosphere;

1: With palladium diacetate; xantphos in N-dodecane; butan-1-ol T=25°C; Suzuki-Miyaura Coupling; 0.0833333 h; Inert atmosphereGlovebox; 2: With cesium hydroxide monohydrate in N-dodecane; water; butan-1-ol T=25°C; Suzuki-Miyaura Coupling; Inert atmosphereGlovebox;

1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethylene glycol dimethyl ether; water / 12 h / Inert atmosphere; Reflux 2.1: trifluoroacetic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice 3.2: 12 h / 20 °C / Inert atmosphere; Cooling with ice 4.1: lithium hydroxide hydrate / tetrahydrofuran; water / 12 h / 60 °C 4.2: 20 °C 5.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.17 h / 100 °C / Inert atmosphere; Microwave irradiation 6.1: pyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice 7.1: triethylsilane; 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 8.1: methanol; trifluorormethanesulfonic acid; trimethyl orthoformate / nitromethane / 1 h / 100 °C / Inert atmosphere; Cooling with ice View Scheme

1: With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane; water; toluene T=100°C; 3 h; 2: With sodium methylate in 1,4-dioxane; water; toluene T=100°C; 0.416667 h;