Iodoethane → Ethyl 4-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 596761Notes

Reaction equation

HRID 596761 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:17])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:24](I)[CH3:25]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:17][CH2:24][CH3:25])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469631HCID 178469631, compound

Product 1

HCID 13072976Ethyl 4-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a solution of 259 g. (1.1 mol.) of 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester in 1700 ml. of dimethylformamide, 400 g. of well powdered potassium carbonate and 300 g. of ethyl iodide are introduced. The reaction mixture is stirred for 7 hours at 65° and filtered under suction, while hot, from excess potassium carbonate. Upon standing overnight, 165 g. of 4-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester crystallize out of the solution, m.p. 112°-115°. After evaporation of the mother liquor, an additional 80 g. are obtained. The total yield amounts to 85% of theory. The compound is recrystallized from benzene (90°-100°), m.p. 113°-115°.

Workup

  1. filtrationfiltered under suction
  2. waitUpon standing overnight
  3. customof 4-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester crystallize out of the solution, m.p. 112°-115°
  4. customAfter evaporation of the mother liquor
  5. customare obtained
  6. customThe total yield
  7. customThe compound is recrystallized from benzene (90°-100°), m.p. 113°-115°

Sources & evidence

ORD record
ord-32427fdcc7ec4463be6e8c274b19c785
Source dataset
uspto-grants-1977_03
Patent number
US04012373

Reaction notes

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