1.1: water; hydrogen bromide / 3 h / 110 °C 1.2: pH 11 / Cooling with ice 2.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 3.1: N-bromosuccinmide / N,N-dimethyl-formamide / 4 h / 20 °C 4.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / ethylene glycol dimethyl ether / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme

water T=95 - 100°C; 4 h; Acidic conditions;

hydrogenchloride; sodium hydroxide

1: 2-methoxy-5-bromo-pyridine With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran; toluene T=25 - 30°C; 9 h; Inert atmosphereLarge scale; 2: alpha-chloropyridine With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in tetrahydrofuran; toluene T=45 - 50°C; 5.5 h; Inert atmosphereLarge scale; SolventTime;

1: 2-methoxy-5-bromo-pyridine With n-butyllithium in tetrahydrofuran; hexane T=-76 - -71°C; 4.5 h; 2: 2-benzenesulfonyl pyridine in tetrahydrofuran; hexane T=-76 - -71°C; 9.5 h;

in methanol; toluene T=10 - 75°C; 3.5 h;

palladium diacetate; potassium carbonate; triphenylphosphine in ethylene glycol dimethyl ether; water Suzuki-Miyaura Coupling; 5.66667 h; Reflux;

ammonium hydroxide; ammonium chloride; potassium carbonate; triphenylphosphine; palladium diacetate in water; ethyl acetate

1: 2-methoxy-5-bromo-pyridine With tris-(dibenzylideneacetone)dipalladium(0); (1-Ad)2P(O)H in tetrahydrofuran Kumada-Corriu coupling reaction; 0.0833333 h; Inert atmosphere; 2: (pyridin-2-yl)magnesium bromide in tetrahydrofuran T=60°C; Kumada-Corriu coupling reaction; 20 h; Inert atmosphere; chemoselective reaction;

1.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C 1.2: 65 percent / triisopropylborate / diethyl ether; hexane / 1 h / -78 °C 2.1: 50 percent / aq. Na2CO3 / Pd(PPh3)4 / dimethylformamide / 22 h / 80 °C View Scheme