1: SnCl2; concentrated aqueous HCl 2: sodium nitrite; aqueous hydrobromic acid / Erhitzen der erhaltenen Diazoniumsalz-Loesung mit Kupfer(I)-bromid und wss. Bromwasserstoffsaeure 3: tetrachloro-<1,4>benzoquinone; xylene View Scheme

in diethyl ether

1: N,N-dimethyl-formamide / 3.5 h / 0 °C / |Inert atmosphere 2: sodium hydroxide; water / 2.5 h / |Reflux View Scheme

N,N,N',N,-tetramethylethylenediamine; palladium diacetate; sodium carbonate; 1,2-bis-(diphenylphosphino)ethane; potassium iodide in N,N-dimethyl-formamide T=130°C; 22 h; Inert atmosphere;

tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate in water; tert-butyl alcohol T=85°C; 10 h; Schlenk techniqueInert atmosphere;

1: 1-methyl-5-bromoindole With magnesium; lithium chloride in tetrahydrofuran T=20°C; Inert atmosphere; 2: N-cyano-N-phenyl-p-methylbenzenesulfonamide in tetrahydrofuran T=0 - 20°C; Inert atmosphere;

1: 1-methyl-5-bromoindole With magnesium in tetrahydrofuran T=120°C; 0.5 h; Inert atmosphereSealed vialMicrowave irradiation; 2: N,N-dimethyl-formamide in tetrahydrofuran T=0 - 20°C;

triethylamine; palladium diacetate; 2-dicyclohexylphosphino-1,1'-biphenyl in 1,4-dioxane T=80°C;

1: Me2PhSiBpin With potassium methanolate in ethylene glycol dimethyl ether T=30°C; 0.166667 h; Inert atmosphere; 2: 1-methyl-5-bromoindole in ethylene glycol dimethyl ether T=30°C; 1 h;

palladium diacetate; triethylamine in 1,4-dioxane under Ar atm.; Schlenk flask charged with Pd(CH3COO)2 and P(C6H11)2(C6H4C6H5); evapd.; filled (Ar); 1,4-dioxane added; stirred for 30 min at room temp.; Et3N added; soln. of bromoindole in dioxane added; neat pinacolborane added; stirred at 80°C; cooled to room temp.; Celite and activated charcoal added; stirred for 15 min; filtered; solvent removed (vac.); residue diluted (cyclohexane); filtered through a short pad of neutral alumina; purified by column chromy (SiO2, cyclohexane/ethyl acetate);