1: 2-fluoro-pyridine With (trimethyl)silylmethyllithium; diisopropylamine in tetrahydrofuran; hexane T=-50°C; 3 h; 2: 1-piperidinecarboxaldehyde in tetrahydrofuran; hexane T=-50 - 20°C;

1: 2-fluoro-pyridine With n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-78 - 0°C; 1 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-55 - 20°C; 0.166667 h; 3: With sodium hydrogencarbonate; ammonium chloride more than 3 stages;

phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide 1.5 h; Ambient temperature;

Pd-BaSO4; hydrogen Rosenmund reduction;

1: 36 percent / NaNO2, HBF4 / 0 deg C to rt 2: 30 percent / KMnO4 / H2O / Heating 3: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 4: 67 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

1: 30 percent / KMnO4 / H2O / Heating 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 3: 67 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

1: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 2: 67 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

Yield given. Multistep reaction;

1: hydrazine hydrate / ethanol / 1 h / 80 °C 2: N-bromosuccinmide / N,N-dimethyl-formamide / 1.67 h / 44 °C View Scheme

1: hydrazine hydrate / ethanol / 1 h / 80 °C 2: N-bromosuccinmide / N,N-dimethyl-formamide / 1.67 h / 44 °C 3: sodium hydride / N,N-dimethyl-formamide / 20 °C / Cooling with ice 4: potassium acetate / 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1.5 h / 100 °C / Inert atmosphere View Scheme