Reaktion #157056

Reaktionsgleichung

4-chloro-3-nitro pyridine

cyclohexenyl boronic acid

→

4-cyclohexenyl-3-nitropyridine

Ausbeute 82.0%

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUpon cooling the reaction
2. 2
   Sonstigewas partitioned between EtOAc and H2O
3. 3
   Waschenwas washed with NaCl(sat.)
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationwas filtered
6. 6
   Sonstigethe volatiles were removed in vacuo
7. 7
   SonstigeThe material was purified by SiO2 chromatography (20% EtOAc/hexanes eluant)

Vorschrift

A solution of 4-chloro-3-nitro pyridine (1 eq.), cyclohexenyl boronic acid (1.7 eq.), and Pd(dppf)Cl2—CH2Cl2 (0.05 eq) in 3:1 DME/2M Na2CO3, at a concentration of 0.1 M was heated at 95° C. for 16 hours. Upon cooling the reaction was partitioned between EtOAc and H2O, was washed with NaCl(sat.), dried over MgSO4, was filtered and the volatiles were removed in vacuo. The material was purified by SiO2 chromatography (20% EtOAc/hexanes eluant) to yield 4-cyclohexenyl-3-nitropyridine (82%). LCMS (m/z): 205.0 (MH+); LC Rt=3.84 min.

Quelle