Reaktion #1713705

Reaktionsgleichung

2-Chloro-6-(trifluoromethyl)nicotinaldehyde

cyclopropylboronic acid

sodium carbonate

→

2-cyclopropyl-6-(trifluoromethyl)nicotinaldehyde

Ausbeute 71.9%

Lösungsmittel

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction
2. 2
   Sonstigevial was purged with argon
3. 3
   Temperaturto cool
4. 4
   Wascheneluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

Vorschrift

2-Chloro-6-(trifluoromethyl)nicotinaldehyde (176 mg, 0.840 mmol), cyclopropylboronic acid (152 mg, 1.76 mmol), sodium carbonate (267 mg, 2.52 mmol) and tetrakis(triphenylphosphine)palladium (0) (48.5 mg, 0.0420 mmol) were combined, diluted with toluene (2 mL) and water (200 μL). The reaction vial was purged with argon, heated to 90° C. and stirred for 24 hours. The reaction was allowed to cool, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 2-cyclopropyl-6-(trifluoromethyl)nicotinaldehyde (130 mg, 0.604 mmol, 71.9% yield).

Quelle