1: 87 percent / NaNO2, HBF4 (34percent) / H2O / 0.5 h / -8 - -2 °C 2: 115 - 120 °C View Scheme

1.1: potassium carbonate / 1 h / 20 °C / |Reflux 2.1: iron; acetic acid / 1 h / 20 °C 2.2: Py*HBr*Br2 / 20 °C View Scheme

1: 80 percent / hydrazine hydrate / ethanol / 1 h / 0 °C 2: 57 percent / 8 h / Heating 3: H2 / Pd-C, 10percent / ethanol / 1 h 4: 20 percent / PPA / 0.12 h / 120 °C View Scheme

potassium carbonate in ethanol 2 h; Reflux;

1: tetrahydrofuran / 20 °C / |Inert atmosphere 2: acetic acid; iron / 3 h / 90 °C / |Inert atmosphere 3: 24 h / 120 °C / |Inert atmosphere 4: tert.-butyl lithium; carbon tetrabromide / -78 °C 5: tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine; potassium phosphate / 1,4-dioxane / 1 h / 120 °C / |Inert atmosphere; |Microwave irradiation 6: hydrogenchloride / tetrahydrofuran / 20 °C / |Inert atmosphere View Scheme

potassium carbonate T=20°C; 1 h; Reflux;

1: 77 percent / ethanol / 16 h / Heating 2: H2 / Pd-C, 10percent / ethanol / 1 h 3: 50 percent / PPA / 120 °C View Scheme

1: (1R)-1-(2,6-dichloro-3-fluorophenyl)ethanol With sodium hydride in tetrahydrofuran; mineral oil T=0 - 20°C; 2.5 h; 2: 2-nitro-3-fluoropyridine in tetrahydrofuran; mineral oil T=0 - 20°C; 3.3 h;

hydrazine hydrate in ethanol T=0°C; 1 h;

1: 77 percent / NaH / tetrahydrofuran / 2 h / 20 °C 2: 83 percent / H2 / Pd/C / methanol / 12 h / 20 °C View Scheme