tetrabutyl ammonium fluoride in tetrahydrofuran 4 h; Reflux;

1: 1-(phenylsulfonyl)-1H-indole With lithium diisopropyl amide in tetrahydrofuran; cyclohexane T=0°C; Metallation; 0.5 h; 2: With zinc(II) chloride in tetrahydrofuran; cyclohexane T=20°C; ion metal exchange; 0.5 h; 3: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride; diisobutylaluminium hydride in tetrahydrofuran; hexane; cyclohexane Arylation; 6 h; Heating; Further stages.;

sodium hydride in tetrahydrofuran T=0 - 10°C;

copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) T=100°C; Stille coupling; 6 h;

1.1: 76 percent / aq. NaOH; tetrabutylammonium bromide / benzene / 2 h / 20 °C 2.1: LDA / tetrahydrofuran; cyclohexane / 0.5 h / 0 °C 2.2: ZnCl2 / tetrahydrofuran; cyclohexane / 0.5 h / 20 °C 2.3: 97 percent / Pd(PPh3)2Cl2; diisobutylaluminum hydride / hexane; tetrahydrofuran; cyclohexane / 6 h / Heating View Scheme

1.1: 76 percent / aq. NaOH; tetrabutylammonium bromide / benzene / 2 h / 20 °C 2.1: LDA / tetrahydrofuran; cyclohexane / 0.5 h / 0 °C 2.2: ZnCl2 / tetrahydrofuran; cyclohexane / 0.5 h / 20 °C 2.3: 97 percent / Pd(PPh3)2Cl2; diisobutylaluminum hydride / hexane; tetrahydrofuran; cyclohexane / 6 h / Heating View Scheme

bis-triphenylphosphine-palladium(II) chloride; diisobutylaluminium hydride in tetrahydrofuran Heating;

bis-triphenylphosphine-palladium(II) chloride; diisobutylaluminium hydride in tetrahydrofuran Heating;

zinc; tetrakis(triphenylphosphine) palladium(0) 1.) THF, r.t., 2 h; 2.) THF, r.t., 18 h; Yield given. Multistep reaction;

1: 65 percent / zinc chloride / triethylene glycol / 8 h / 190 °C / microwave irradiation 2: 74 percent / sodium hydride / tetrahydrofuran / 0 - 10 °C View Scheme