Reacción #67743

Ecuación de reacción

1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid

thionyl chloride

5-bromopyridin-2-amine

→

1-(benzo[d][1,3]dioxol-5-yl)-N-(5-bromopyridin-2-yl)cyclopropanecarboxamide

Rendimiento 81.3%

Disolventes

pyridine

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe excess thionyl chloride was evaporated under reduced pressure
2. 2
   workup.STIRRINGThe reaction mixture was stirred at 110° C. for one hour and thirty minutes
3. 3
   OtroThe pyridine was evaporated under reduced pressure
4. 4
   workup.DISSOLUTIONThe resulting mixture was dissolved in dichloromethane (100 mL)
5. 5
   Lavadowashed with 1N NaOH (3×25 mL)
6. 6
   SecadoThe organic layer was dried over anhydrous Na2SO4
7. 7
   Otroevaporated under reduced pressure
8. 8
   OtroThe crude product was purified by column chromatography on silica gel

Procedimiento

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid (9.50 g, 46.00 mmol), thionyl chloride (10.00 mL, 138.00 mmol) and DMF (4 drops) were added and the reaction mixture was stirred and heated at 60° C. for thirty minutes. The excess thionyl chloride was evaporated under reduced pressure. A portion of the acid chloride (14.4 mmol) was dissolved in pyridine (10 mL) and was slowly added to 5-bromopyridin-2-amine (14.4 mmol) in pyridine (10 mL). The reaction mixture was stirred at 110° C. for one hour and thirty minutes. The pyridine was evaporated under reduced pressure. The resulting mixture was dissolved in dichloromethane (100 mL) and washed with 1N NaOH (3×25 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-bromopyridin-2-yl)cyclopropanecarboxamide (4.20 g, 11.7 mmol, 81%).

Fuente