Isopropanol → 3-ethyl-5-methyl-7-(1-methylethoxy)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

HRID 371929Notes

Reaction equation

HRID 371929 reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:6])[CH3:5].Cl[C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH3:19])[N:11]=[C:10]2[N:20]([CH2:23][CH3:24])[CH:21]=[N:22][C:9]=12>C1C=CC=CC=1>[CH2:23]([N:20]1[C:10]2=[N:11][C:12]([CH3:19])=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]([O:6][CH:4]([CH3:5])[CH3:3])=[C:9]2[N:22]=[CH:21]1)[CH3:24]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 123876387-chloro-3-ethyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

Product 1

HCID 123876423-ethyl-5-methyl-7-(1-methylethoxy)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.03 g. of sodium hydride and 0.6 g. of propane-2-ol are refluxed with stirring in 50 ml. dry benzene for 10 hours. After this time, 2.7 g. of 7-chloro-3-ethyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester obtained in Example 1 d are added and heating is continued for an additional 10 hours. The inorganic precipitate is filtered off and the solvent removed by distillation. The oily residue is distilled to obtain 3-ethyl-5-methyl-7-(1-methylethoxy)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester, b.p. 180°-185°/0.05. Yield 2 g. (69%).

Workup

  1. customobtained in Example 1 d
  2. additionare added
  3. temperatureheating
  4. filtrationThe inorganic precipitate is filtered off
  5. customthe solvent removed by distillation
  6. distillationThe oily residue is distilled

Sources & evidence

ORD record
ord-9c929e38188842efb7fb40504bb9f30b
Source dataset
uspto-grants-1978_05
Patent number
US04088654

Reaction notes

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