(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate in 1,4-dioxane T=60°C; Miyaura reaction; RefluxInert atmosphere;

1: 2-lt;lt;(tert-butyldimethylsilyl)oxygt;methylgt;-5-bromopyridine With n-butyllithium; tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - 0°C; 3 h; Inert atmosphere; 2: 2,3-dimethylbutane-2,3-diol in benzene Inert atmosphereDean-StarkReflux;

1.1: n-butyllithium / toluene; hexane / 0.17 h / -78 °C / |Inert atmosphere 1.2: 3 h / -78 °C / |Inert atmosphere 2.1: sodium tetrahydroborate; methanol / 0 - 20 °C / |Inert atmosphere 3.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / 20 °C / |Inert atmosphere 4.1: n-butyllithium; tri-isopropoxy-borane / hexane; tetrahydrofuran / 3 h / -78 - 0 °C / |Inert atmosphere 4.2: |Inert atmosphere; |Dean-Stark; |Reflux View Scheme

1.1: sodium tetrahydroborate; methanol / 0 - 20 °C / |Inert atmosphere 2.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / 20 °C / |Inert atmosphere 3.1: n-butyllithium; tri-isopropoxy-borane / hexane; tetrahydrofuran / 3 h / -78 - 0 °C / |Inert atmosphere 3.2: |Inert atmosphere; |Dean-Stark; |Reflux View Scheme

1.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / 20 °C / |Inert atmosphere 2.1: n-butyllithium; tri-isopropoxy-borane / hexane; tetrahydrofuran / 3 h / -78 - 0 °C / |Inert atmosphere 2.2: |Inert atmosphere; |Dean-Stark; |Reflux View Scheme