Reaction #502136

Reaction equation

methyl (2-bromophenyl)acetate

6-methoxypyridin-3-ylboronic acid

caesium fluoride

1,2-dimethoxyethane

→

Methyl[2-(6-methoxypyridin-3-yl)phenyl]acetate

Solvents

ethyl acetate

water

ethyl acetate

Conditions

Workup

1. 1
   TemperatureCooling to room temperature
2. 2
   DryingAfter the organic phase has been dried over magnesium sulphate
3. 3
   Otherthe solvent has been removed in vacuo
4. 4
   Otherthe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1)
5. 5
   Other1.1 g (68% of theory) of the product are obtained

Procedure

1.35 g (5.89 mmol) of methyl (2-bromophenyl)acetate are introduced together with 1 g (6.55 mmol) of 6-methoxypyridin-3-ylboronic acid and 1.98 g (13.09 mmol) of caesium fluoride into 20 ml of 1,2-dimethoxyethane under argon. After addition of 0.22 g (0.19 mmol) of tetrakis(triphenylphosphine)palladium(0), the reaction mixture is stirred at 100° C. for 4 h. Cooling to room temperature is followed by addition of a mixture of ethyl acetate and water and extraction with ethyl acetate. After the organic phase has been dried over magnesium sulphate and the solvent has been removed in vacuo, the residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). 1.1 g (68% of theory) of the product are obtained.

Source