Reaktion #974894

Reaktionsgleichung

toluene

3-Amino-6-chloro-2-iodo-4-methylpyridine

2-furanboronic acid

sodium carbonate

→

title compound

Ausbeute 86.6%

3-amino-6-chloro-2-(2-furanyl)-4-methylpyridine

Ausbeute 86.6%

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   Sonstigeevaporation
3. 3
   Sonstigeflushing with nitrogen (5×) and tetrakis(triphenylphosphine)palladium(0) (658 mg)
4. 4
   workup.ADDITIONwas added
5. 5
   workup.ADDITIONAfter addition of another portion of 2-furanboronic acid (430 mg) and tetrakis(triphenyl phosphine)palladium(0) (132 mg)
6. 6
   workup.STIRRINGthe mixture was stirred again for 12 hours at 90° C
7. 7
   workup.STIRRINGAfter 12 hours stirring at room temperature
8. 8
   Sonstigethe reaction mixture was quenched with water
9. 9
   Extraktionextracted 2× with ethyl acetate
10. 10
    WaschenThe combined organic layer was washed with brine
11. 11
    Trocknendried over MgSO4
12. 12
    Einengenconcentrated in vacuum
13. 13
    SonstigeThe residue was purified by column chromatography (silica 60, hexane/ethyl acetate=4:1, Rf=0.25)

Vorschrift

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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