Réaction #163564

Équation de réaction

5-bromo-pyridine-2-carboxylic acid

4-(2-carboxyethyl)benzeneboronic acid

sodium carbonate

→

5-[4-(2-Carboxy-ethyl)-phenyl]-pyridine-2-carboxylic acid

Solvants

1,2-dimethoxyethane

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   Autrequenched with water
3. 3
   workup.ADDITIONEthyl acetate is added
4. 4
   ExtractionAfter threefold extraction with ethyl acetate
5. 5
   Séchagethe combined organic layers are dried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated in vacuo
8. 8
   AutreThe residue is purified by silica gel chromatography (eluent:dichloromethane/methanol 5:1)

Mode opératoire

Under an argon atmosphere, to 4 ml 1,2-dimethoxyethane are added 5-bromo-pyridine-2-carboxylic acid (93 mg, 0.46 mmol), 4-(2-carboxyethyl)benzeneboronic acid (106 mg, 0.55 mmol), 0.51 ml of a 2M aqueous sodium carbonate solution and dichlorobis-(triphenylphosphin) palladium (II) (20 mg, 0.03 mmol). The mixture is stirred at 90° C. overnight, cooled and quenched with water. Ethyl acetate is added and the mixture adjusted to pH=2 with 1M hydrochloric acid. After threefold extraction with ethyl acetate, the combined organic layers are dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue is purified by silica gel chromatography (eluent:dichloromethane/methanol 5:1).

Source