Reaction #74058

Reaction equation

2,3-dichloropyrazine

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile

sodium carbonate

→

4-(3-chloropyrazin-2-yl)-1-naphthonitrile

Solvents

dioxane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture cooled to room temperature
2. 2
   Washwashed with water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Otherpurified by chromatography

Procedure

A mixture of 2,3-dichloropyrazine (2.98 g, 2 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile (0.558 mmol, 2 mmol) palladium tetrakis triphenylphoshine (0.069 g, 0.06 mmol) and aqueous sodium carbonate solution (2M, 3 mL, 6 mmol) in dioxane (7 mL) was heated to 80° C. for 12 hours. The reaction mixture cooled to room temperature, washed with water, extracted with ethyl acetate and purified by chromatography to yield 4-(3-chloropyrazin-2-yl)-1-naphthonitrile (0.36 g, 68%).

Source