Reacción #1014751

Ecuación de reacción

5-bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

cyclopropylboronic acid

potassium phosphate

→

title compound

Rendimiento 142.9%

5-Cyclopropyl-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

Rendimiento 142.9%

Disolventes

toluene

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONdissolved in water
3. 3
   Extracciónextracted with ethyl acetate (3×30 mL)
4. 4
   Lavadowashed with brine
5. 5
   Secadodried (sodium sulfate)
6. 6
   Otroevaporated to dryness
7. 7
   OtroThe residue was purified by column chromatography (silica gel, 10 g, 5% ethyl acetate in petroleum ether)

Procedimiento

Under an atmosphere of nitrogen, a solution of 5-bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester (0.2 g, 0.7 mmol), cyclopropylboronic acid (CAN 411235-57-9, 81 mg, 0.9 mmol), palladium acetate (CAN 3375-31-3, 8 mg, 0.037 mmol), tricyclohexylphosphine (CAN 2622-14-2, 0.021 g, 0.07 mmol) and potassium phosphate (0.54 g, 0.20 mmol) in toluene (20 mL) and water (1 mL) was heated to 110° C. for 48 h. The reaction mixture was concentrated under reduced pressure, dissolved in water, extracted with ethyl acetate (3×30 mL), washed with brine, dried (sodium sulfate) and evaporated to dryness. The residue was purified by column chromatography (silica gel, 10 g, 5% ethyl acetate in petroleum ether) to yield the title compound (0.16 g, 1 mmol, 93%) as yellow oil; MS (EI): m/e 252.2 [M+H]+.

Fuente