Reaktion #345269

ord-6a4dc4231a9f47f289fae809b6ac5f97

Reaktionsgleichung

c1ccc(-c2n[nH]c3ccncc23)cc1
3-Phenyl-1H-pyrazolo[4,3-c]pyridine
ClCCn1ccnc1
1-(2-chloroethyl)imidazole
O=C([O-])[O-].[K+].[K+]
K2CO3
O=C([O-])[O-].[K+].[K+]
K2CO3
O
H2O
CCOC(C)=O
ethyl acetate
ClCCn1ccnc1
1-(2-chloroethyl)imidazole
→
O=C(CCn1nc(-c2ccccc2)c2cnccc21)c1ncc[nH]1
product
O=C(CCn1nc(-c2ccccc2)c2cnccc21)c1ncc[nH]1
1-[2-(1H-Imidazoyl)ethyl]-3-phenyl-1H-pyrazolo[4,3-c]pyridine

Edukte

c1ccc(-c2n[nH]c3ccncc23)cc1
3-Phenyl-1H-pyrazolo[4,3-c]pyridine
ClCCn1ccnc1
1-(2-chloroethyl)imidazole
O=C([O-])[O-].[K+].[K+]
K2CO3
O=C([O-])[O-].[K+].[K+]
K2CO3
O
H2O
CCOC(C)=O
ethyl acetate
ClCCn1ccnc1
1-(2-chloroethyl)imidazole

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
N,N-dimethylformamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONhad been added
  2. 2
    Temperaturwarmed at 90° for 2 hours
  3. 3
    Waschenthe organic phase was washed with water
  4. 4
    SonstigeEvaporation and trituration with ether

Vorschrift

3-Phenyl-1H-pyrazolo[4,3-c]pyridine (2.93 g) was suspended in 30 ml of N,N-dimethylformamide to which 1-(2-chloroethyl)imidazole (2.15 g) and K2CO3 (2.3 g) had been added. This mixture was stirred and warmed at 90° for 2 hours and then an additional 0.20 g of 1-(2-chloroethyl)imidazole and 0.2 g of K2CO3 were added. After an additional 45 minutes, the reaction mixture was distributed between H2O and ethyl acetate and the organic phase was washed with water. Evaporation and trituration with ether gave 2.15 g of product after recrystallization from CH2Cl2 -pentane, mp 123°-125°.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05264576uspto-grants-1993_11