Reaction #74063

Reaction equation

4-chloro-5-bromopyrimidine

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

sodium carbonate

→

4-(5-bromopyrimidin-4-yl)-1-naphthonitrile

Yield 69.0%

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 4-chloro-5-bromopyrimidine (193 mg, 1 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile (279 mg, 1 mmol) palladium tetrakis triphenylphoshine (0.023 g, 0.02 mmol) and aqueous sodium carbonate solution (2M, 1.5 mL, 3 mmol) in dioxane (3 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-(5-bromopyrimidin-4-yl)-1-naphthonitrile (214 mg, 69%).

Source