Sodium hydride → ethyl 4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate

HRID 1088222Notes

Reaction equation

HRID 1088222 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[H-].[Na+].[H][H].Br[CH2:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1>CN(C)C=O.C(OCC)(=O)C>[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]([CH2:15][C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 178418361HCID 178418361, compoundHCID 178419860HCID 178419860, compound

Product 1

HCID 14369745ethyl 4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of imidazo[4,5-c]pyridine (10.0 g. 0.084 mol) in dry dimethylformamide (100 ml) at 18° C. under a nitrogen atmosphere, was treated with sodium hydride (5.04 g of 60% dispersion in mineral oil, 0.126 mol) in portions over a period of 5 minutes. The mixture was stirred for an additional 2.5 hours until hydrogen evolution had ceased. The mixture was cooled to 0° C., treated with ethyl 4-bromomethylbenzoate (22.6 g, 0.093 mol), allowed to warm up to room temperature and then stirred for an additional 18 hours. The mixture was diluted with ethyl acetate (600 ml), washed with water (3×200 ml) and dried over anhydrous sodium sulphate. The solvent was evaporated off under reduced pressure to yield an impure mixture of isomers which was purified by chromatography (silica gel, chloroform) to yield a less polar isomer which was recrystallized from ethyl acetate-hexane to yield ethyl 4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate as a colorless crystalline solid, having a melting point of 110°-111.5° C. and the following physical characteristics:

Workup

  1. temperatureto warm up to room temperature
  2. washwashed with water (3×200 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customThe solvent was evaporated off under reduced pressure
  5. customto yield
  6. additionan impure mixture of isomers which
  7. customwas purified by chromatography (silica gel, chloroform)
  8. customto yield a less polar isomer which
  9. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ebf19c99893c4e859a08eb410d2f8dfe
Source dataset
uspto-grants-1990_10
Patent number
US04962106

Reaction notes

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