1: With triethylamine in benzene 2 h; 2: in bis-maleimidodiphenyl-methane acid T=90°C; 3.5 h; Reflux;

1: With potassium 2-methyl-2-butoxide in toluene T=85°C; Heating; 2: With hydrogenchloride in 1-methyl-pyrrolidin-2-one; water Inert atmosphere;

oxygen; Trimethylene glycol; copper(l) chloride; palladium dichloride in ethylene glycol dimethyl ether

1: 67.7 percent / 2.25 h 2: 63 percent / konz. HCl / ethanol / Heating View Scheme

N-bromosuccinmide in acetonitrile 3.5 h; RefluxInert atmosphere;

1.1: N-bromosuccinmide / acetonitrile / 3.5 h / |Reflux; |Inert atmosphere 2.1: trichlorophosphate / 5 h / |Reflux; |Inert atmosphere 3.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / |Inert atmosphere 3.2: 0.75 h / 65 °C / |Inert atmosphere 3.3: 0.5 h / -60 - -40 °C 4.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C / |Inert atmosphere 5.1: potassium tert-butylate / dimethyl sulfoxide / 3.5 h / 10 - 20 °C / |Sonication; |Inert atmosphere 6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / |Inert atmosphere 7.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / |Inert atmosphere View Scheme

methanesulfonic acid; [bis(acetoxy)iodo]benzene Inert atmosphereCooling with iceReflux;

1.1: N-bromosuccinmide / acetonitrile / 3.5 h / |Reflux; |Inert atmosphere 2.1: trichlorophosphate / 5 h / |Reflux; |Inert atmosphere 3.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / |Inert atmosphere 3.2: 0.75 h / 65 °C / |Inert atmosphere 3.3: 0.5 h / -60 - -40 °C 4.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C / |Inert atmosphere View Scheme