6-Bromo-5-methylpyridine-3-boronic acid

To a reaction vessel (lOOmL) in a nitrogen atmosphere containing 6 (i.4g, 3.6mmol) were added 6-bromo-5methy1pyridin-3-ylboronic acid 7 (978mg, 4.5mmol), tetrakis triphenylphosphine (210mg, 0.l8mmol), potassium phosphate (2.lg, 9mmol) in 1, 2-dimethoxyethane (3OmL). The mixture was stirred at reflux for 20 hours until consumption of starting material followed by TLC. At room temperature, the solution was extracted with ethyl acetate. The organic layer was dried on MgSO4, filtered and evaporated. The residue was purified by chromatography (chexane:ethyl acctate95:5, then 9:1 and 8:2) and 5, 6t dibromo-5?-methyl-3-((E)-styryl)-2, 3?-bipyridine 8 (yield: 86%) was obtained.To a reaction vessel in a nitrogen atmosphere containing (E)-5-bromo-2-iodo-3-styrylpyridine 1 (3.0g, 7.7mmol) in 200mL of 123 1, 4-dioxane, were added 55 To a reaction vessel in a nitrogen atmosphere containing (E)-6-iodo-5-styryl-3, 3?-bipyridine 9 (1.5g, 3.9mmol) in 200mL of 1, 4-dioxane, were added To a glass vial containing a magnetic stirring bar was added