Reacción #1269882

Ecuación de reacción

water

4-bromonicotinaldehyde

phenylboronic acid

Na2CO3

→

4-phenylnicotinaldehyde

Rendimiento 50.5%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónfollowed by extraction with EtOAc
2. 2
   Filtraciónthe combined organic layers were filtered (celite)
3. 3
   Secadodried (MgSO4)
4. 4
   OtroPurification by flash chromatography (heptane/EtOAc, gradient 5-40% EtOAc)

Procedimiento

4-bromonicotinaldehyde (150 mg, 0.81 mmol), phenylboronic acid (98 mg, 0.81 mmol) and tetrakis(triphenylphosphine)palladium(0) (46.6 mg, 0.05 mmol) were mixed in dioxane (3.5 mL). Na2CO3 (2 M solution in water, 0.81 mL, 1.63 mmol) was added and the reaction mixture was stirred and heated in the microwave (110° C., 150 W) for 30 min. After addition of excess water followed by extraction with EtOAc, the combined organic layers were filtered (celite) and dried (MgSO4). Purification by flash chromatography (heptane/EtOAc, gradient 5-40% EtOAc) provided 4-phenylnicotinaldehyde (75 mg, 48%) as a dark yellow gum. ESI-MS [M+H]+=279.1.

Fuente