Iodoethane → 4-Ethoxy-1-(2-furyl)methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

HRID 1576090Notes

Reaction equation

HRID 1576090 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:28](I)[CH3:29]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:21][CH2:28][CH3:29])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469629HCID 178469629, compound

Product 1

HCID 544738334-Ethoxy-1-(2-furyl)methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 g of 4-hydroxy-1-(2-furyl)methyl-1H-pyrazolo[3,4-b]-pyridine-5-carboxylic acid ethyl ester (1.05 mol) is dissolved in 1 liter of dimethylformamide. 210 g of potassium carbonate (1.5 mol) and 233 g of ethyl iodide are added. The mixture is heated at 60° with continuous stirring for 10 hours. The excess potassium carbonate is filtered off. On addition of 500 ml of water, 4-ethoxy-1-(2-furyl)methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester precipitates and is recrystallized from methanol, yield 280 g (85%), m.p. 93°-96°.

Workup

  1. temperatureThe mixture is heated at 60°
  2. filtrationThe excess potassium carbonate is filtered off
  3. additionOn addition of 500 ml of water, 4-ethoxy-1-(2-furyl)methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester
  4. customprecipitates
  5. customis recrystallized from methanol, yield 280 g (85%), m.p. 93°-96°

Sources & evidence

ORD record
ord-93c363d16eb54bc5a59b0a77c5e076f6
Source dataset
uspto-grants-1976_09
Patent number
US03979399

Reaction notes

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