1.1: 3 h / 110 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C 2.2: -78 - 20 °C 3.1: caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 90 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.03 h 5.1: N-iodo-succinimide / acetonitrile / 0.83 h / 0 °C 6.1: tris-(dibenzylideneacetone)dipalladium(0) / isobutyramide / 6 h / 60 °C / Inert atmosphere 7.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C 8.1: sodium hydroxide; water / ethanol / 3 h / 60 °C 9.1: 4-(N,N-dimethlyamino)pyridine; 4-methyl-morpholine; HATU / acetonitrile / 5.75 h / 20 - 50 °C 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C 11.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 11.2: 72 h 12.1: acetic acid / 4 h / 35 °C 12.2: 6 h / 60 °C View Scheme

1: With sodium nitrite 2: With hypophosphorous ether T=100°C;

1: (2,6-dichloro-3-nitro-pyridin-4-yl)-methylamine With hydrogenchloride; tin(ll) chloride in methanol; water 1 h; Heating / reflux; 2: trimethyl orthoformate in methanol 1 h; Heating / reflux; Product distribution / selectivity;

in ethanol T=20 - 80°C; 15 h; Product distribution / selectivity;