Water → HCID 22418066, compound

HRID 1728577Notes

Reaction equation

HRID 1728577 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1.[H-].[Na+].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=4[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=3)[C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178439961HCID 178439961, compound

Product 1

HCID 22418066HCID 22418066, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg of the above-prepared 7-chloro-2-n-propyl-3H-imidazo[4,5-b]pyridine and 380 mg of methyl 2-(4-bromomethylphenyl)benzoate were dissolved in dimethylformamide, and 50 mg of sodium hydride was added to the solution. The mixture was stirred at room temperature for 20 min, and water was added thereto, followed by extraction 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=40:1→20:1) to prepare the intended product as a colorless oleaginous substance. The yield was 140 mg.

Workup

  1. extractionfollowed by extraction 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=40:1→20:1)
  5. customto prepare the intended product as a colorless oleaginous substance

Sources & evidence

ORD record
ord-3ee8ffd7e29945dc8e699d7016185c15
Source dataset
uspto-grants-1994_07
Patent number
US05328911

Reaction notes

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