potassium hydroxide in acetone T=0 - 25°C;

1: 6-bromo-1H-indole With sodium hydride in N,N-dimethyl-formamide T=20°C; 0.333333 h; 2: methyl iodide in N,N-dimethyl-formamide T=20°C; 1 h;

in tetrahydrofuran; hexane; mineral oil

1: 5-Bromo-1H-indole With sodium hydride in tetrahydrofuran T=20°C; 1 h; 2: methyl iodide in tetrahydrofuran

1: 6-bromo-1-methyl-1H-indole With n-butyllithium 2: N,N-dimethyl-formamide

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

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);

1: 6-bromo-1-methyl-1H-indole With sec.-butyllithium in diethyl ether T=-78°C; 2: methyl chloroformate in diethyl ether T=-78 - -20°C;

in 1-methyl-pyrrolidin-2-one

N-methyl-pyrrolidine T=150°C; 48 h;