Water → 1-[2-(1H-Imidazoyl)ethyl]-3-phenyl-1H-pyrazolo[4,3-c]pyridine

HRID 487590Notes

Reaction equation

HRID 487590 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:10]=3[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCC[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.[C:24]([O-:27])([O-])=O.[K+].[K+].O.[C:31](OCC)(=O)[CH3:32]>CN(C)C=O>[NH:21]1[CH:22]=[CH:23][N:19]=[C:20]1[C:24]([CH2:31][CH2:32][N:9]1[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1)=[O:27]

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate2×HCID 27575041-(2-Chloroethyl)imidazole2×HCID 138011253-Phenyl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 199304931-[2-(1H-Imidazoyl)ethyl]-3-phenyl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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°.

Workup

  1. additionhad been added
  2. temperaturewarmed at 90° for 2 hours
  3. washthe organic phase was washed with water
  4. customEvaporation and trituration with ether

Sources & evidence

ORD record
ord-8d732942e172422ab0d065635f8b7c2f
Source dataset
uspto-grants-1994_03
Patent number
US05296491

Reaction notes

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