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

HRID 258085Notes

Reaction equation

HRID 258085 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.BrCC[C:19]1[CH:29]=[CH:28][CH:27]=[C:21]2[C:22]([NH:24][C:25](=O)[C:20]=12)=[O:23].[C:30]([O-:33])([O-])=O.[K+].[K+].O.[CH3:37]N(C)C=O>>[C:1]1([C:7]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:10]=3[N:9]([CH2:37][CH2:25][N:24]3[C:22](=[O:23])[C:21]4=[CH:20][CH:19]=[CH:29][CH:28]=[C:27]4[C:30]3=[O:33])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium Carbonate3×HCID 138011253-Phenyl-1H-pyrazolo[4,3-c]pyridineHCID 219600212-Bromoethylphthalimide3×

Product 1

HCID 199304793-phenyl-1-[2-(phthalimido)ethyl]-1H-pyrazolo[4,3-c]pyridine

Conditions

Temperature
90 °C

Procedure

3-Phenyl-1H-pyrazolo[4,3-c]pyridine (1.95 g) was suspended in 50 ml of dimethylformamide to which 2-bromoethylphthalimide (2.54) and K2CO3 (1.4 g) had been added. This mixture was stirred and warmed at 90° C. for 4 hours and then an additional 1.25 g of 2-bromoethylphthalimide and 0.7 g of K2CO3 were added. After 2 more hours another 0.60 g of 2-bromoethylphthalimide and 0.4 g of K2CO3 were added and stirring and heating were continued for an additional 90 minutes. At the end of this time, the reaction mixture was poured into H2O and the product filtered off and dried to give 2.63 of 3-phenyl-1-[2-(phthalimido)ethyl]-1H-pyrazolo[4,3-c]pyridine.

Workup

  1. additionhad been added
  2. stirringstirring
  3. temperatureheating
  4. filtrationthe product filtered off
  5. customdried

Sources & evidence

ORD record
ord-29dc150bddc840d39ceda1865958fdbc
Source dataset
uspto-grants-1993_11
Patent number
US05264576

Reaction notes

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