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

HRID 22470Notes

Reaction equation

HRID 22470 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-ed59b1e807ba42099f1985e5f75dc60f
Source dataset
uspto-grants-1995_06
Patent number
US05428169

Reaction notes

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