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

Temperatur

60 °C

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%).

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

ORD-Eintrag

ord-af36d083591b43ee914efcef6980fcd8

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08524910B2