Water → HCID 22418022, compound

HRID 1728580Notes

Reaction equation

HRID 1728580 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([S:11][CH3:12])=[N:10][C:3]=12.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=1.[H-].[Na+].O>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=4[C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=3)[C:9]([S:11][CH3:12])=[N:10][C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178503344HCID 178503344, compound

Product 1

HCID 22418022HCID 22418022, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg of 7-methyl-2-methylthio-3H-imidazo[4,5-b]-pyridine and 370 mg of methyl 2-(4-bromomethylphenyl)benzoate was dissolved in dimethylformamide, and 48 mg of sodium hydride was added at room temperature to the solution under stirring. The reaction was allowed to proceed for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was distilled off in vacuo. The residue was purified by silica gel chromatography (benzene:ethyl acetate=10:1→3:2) to prepare the intended product as a colorless oleaginous substance. The yield was 60 mg.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. distillationthe solvent was distilled off in vacuo
  4. customThe residue was purified by silica gel chromatography (benzene:ethyl acetate=10:1→3:2)
  5. customto prepare the intended product as a colorless oleaginous substance

Sources & evidence

ORD record
ord-9d730b69b31246b8bba4d52850773017
Source dataset
uspto-grants-1994_07
Patent number
US05328911

Reaction notes

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