Reaction #792216

Reaction equation

water

3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-furyl]pyridine

2-(6-bromopyridin-2-yl)pyrimidine

sodium carbonate

→

2-{6-[5-(pyridin-3-yl)-3-furyl]pyridin-2-yl}pyrimidine

Yield 50.0%

Solvents

dioxane

Conditions

Workup

1. 1
   OtherThe reaction mixture was degassed in an ultrasonic bath under argon
2. 2
   Temperatureheated
3. 3
   Temperatureto reflux temperature
4. 4
   Temperatureunder reflux for 8 hours
5. 5
   Otherat room temperature
6. 6
   Otherovernight
7. 7
   Extractionextracted with dichloromethane
8. 8
   Washwashed with 100 ml of water
9. 9
   Dryingdried over MgSO4
10. 10
    FiltrationThe mixture was then filtered
11. 11
    Concentrationconcentrated under reduced pressure on a rotary evaporator
12. 12
    OtherChromatographic purification

Procedure

400 mg (1.38 mmol) of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-furyl]pyridine and 347 mg (1.38 mmol) of 2-(6-bromopyridin-2-yl)pyrimidine were initially charged in 20 ml of dioxane, and 3.46 ml of a 2 molar aqueous sodium carbonate solution were added. The reaction mixture was degassed in an ultrasonic bath under argon and then heated to reflux temperature, and, at 80° C., 48.0 mg (42.0 μmol) of tetrakis(triphenylphosphine)palladium(0) were added. The reaction mixture was stirred under reflux for 8 hours and then at room temperature overnight. The mixture was then poured into 100 ml of water and extracted with dichloromethane. The light-yellow organic phases were combined, washed with 100 ml of water and then dried over MgSO4. The mixture was then filtered and concentrated under reduced pressure on a rotary evaporator. Chromatographic purification gave 206 mg (50% of theory) of 2-{6-[5-(pyridin-3-yl)-3-furyl]pyridin-2-yl}pyrimidine.

Source