[2,2']bipyridinyl; n-butyllithium 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h; Yield given. Multistep reaction;

water; toluene-4-sulfonic acid 16 h; Heating / reflux;

1.1: oxalyl chloride; DMF / CH2Cl2 / 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / -78 °C 2.2: hexane; tetrahydrofuran; CH2Cl2 / -78 - 10 °C View Scheme

1: diethylmalonate potassium salt With triethylamine; magnesium chloride in acetonitrile T=20 - 25°C; 2: 2,4,5-trifluoro-3-methoxybenzoic acid chloride With triethylamine in acetonitrile T=20°C; 18 h;

1: malonic acid ethyl ester monopotassium salt With magnesium chloride in ethyl acetate T=20°C; 0.5 h; Inert atmosphere; 2: With triethylamine in ethyl acetate T=20°C; 0.5 h; Inert atmosphere; 3: 2,4,5-trifluoro-3-methoxybenzoic acid chloride in ethyl acetate 2 h; Inert atmosphereReflux;

1.1: aq. NaOH / methanol 2.1: (COCl)2; DMF / CH2Cl2 3.1: MgCl2; Et3N / acetonitrile / 20 - 25 °C 3.2: Et3N / acetonitrile / 18 h / 20 °C View Scheme

1: triethylamine; magnesium chloride / ethyl acetate 2: hydrogenchloride; water View Scheme

1: acetic anhydride / 22 h / Heating 2: ethanol / 18 h / Ambient temperature 3: 81 percent / NaH / tetrahydrofuran / 18 h View Scheme

1.1: potassium hydroxide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.5 h / 20 °C / |Inert atmosphere 1.2: 16 h / 0 - 20 °C / |Inert atmosphere 1.3: 3 h / |Inert atmosphere 2.1: potassium tert-butylate / toluene / 16 h / |Inert atmosphere; |Reflux 3.1: Oxonereg; / water; methanol / 3 h / 55 - 60 °C 4.1: sodium hydrogen sulfide hydrate / N,N-dimethyl-formamide / 5 h / 20 °C / |Inert atmosphere 4.2: pH Ca. 1 - 2 5.1: potassium phosphate; hydroxylamine-o-sulphonic acid / water; tetrahydrofuran / 0 - 20 °C View Scheme

1.1: potassium hydroxide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.5 h / 20 °C / |Inert atmosphere 1.2: 16 h / 0 - 20 °C / |Inert atmosphere 1.3: 3 h / |Inert atmosphere 2.1: potassium tert-butylate / toluene / 16 h / |Inert atmosphere; |Reflux 3.1: Oxonereg; / water; methanol / 3 h / 55 - 60 °C 4.1: sodium hydrogen sulfide hydrate / N,N-dimethyl-formamide / 5 h / 20 °C / |Inert atmosphere 4.2: pH Ca. 1 - 2 5.1: potassium phosphate; hydroxylamine-o-sulphonic acid / water; tetrahydrofuran / 0 - 20 °C 6.1: N,N-dimethyl acetamide / 18 h / 90 °C / |Inert atmosphere 7.1: dichloromethane / 4 h / 20 °C / |Inert atmosphere 8.1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 0.17 h / 67 °C / |Inert atmosphere View Scheme