Water → HCID 57941023, compound

HRID 1437470Notes

Reaction equation

HRID 1437470 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][N:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=2)[N:14]=[C:13]1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1)(=O)C.[OH-].[Li+].O>O1CCCC1CO>[CH3:34][O:33][C:29]1[CH:28]=[C:27]([C:13]2[N:12]([CH2:11][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[OH:4])[C:20]3[C:15]([N:14]=2)=[N:16][CH:17]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=3)[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57941013HCID 57941013, compound

Product 1

HCID 57941023HCID 57941023, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

2-[[2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridin-1-yl]methyl]phenyl acetate (Compound of Example 153) (177 mg) was dissolved in tetrahydrofuran-methanol (1:1, v/v, 20 ml). To the solution was added 2 N lithium hydroxide (6.8 ml). The mixture was stirred at room temperature for 1.5 hour. The reaction mixture was poured into water and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure, and the resulting crystals were collected by filtration to obtain 2-[[2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridin-1-yl]methyl]phenol (133 mg, 83%). The crystals were recrystallized from tetrahydrofuran-ethyl acetate.

Workup

  1. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure
  5. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-30113b4124bf47509a72f8287140f086
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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