Toluene → 3-Amino-6-chloro-2-(2-furanyl)-4-methylpyridine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

3-Amino-6-chloro-2-iodo-4-methylpyridine (1.38 g), 2-furanboronic acid (861 mg), and sodium carbonate (815 mg) were suspended in a solvent mixture consistent of toluene (19 mL), THF (19 mL) and water (6 mL). The mixture was degassed using subsequent evaporation and flushing with nitrogen (5×) and tetrakis(triphenylphosphine)palladium(0) (658 mg) was added. The reaction mixture was stirred at 90° C. for 5 hours and 12 hours at room temperature. After addition of another portion of 2-furanboronic acid (430 mg) and tetrakis(triphenyl phosphine)palladium(0) (132 mg), the mixture was stirred again for 12 hours at 90° C. After 12 hours stirring at room temperature, the reaction mixture was quenched with water and extracted 2× with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate=4:1, Rf=0.25) to afford 929 mg of the title compound of the formula

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