Water → 5-[2-(p-[Ethoxycarbonylmethoxy]phenyl)ethen-1-yl]imidazo[1,5-a]pyridine

HRID 280228Notes

Reaction equation

HRID 280228 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C)C=O>[CH2:26]([O:25][C:23]([CH2:22][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1)=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 540585275-[2-(p-Hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine

Product 1

HCID 538749585-[2-(p-[Ethoxycarbonylmethoxy]phenyl)ethen-1-yl]imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-[2-(p-hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine (2.36 g) in 10 ml of dimethylformamide is added to a slurry of 0.5 g of sodium hydride in 30 ml of dry dimethylformamide at 0° under nitrogen. After warming to room temperature ethyl bromoacetate (1.67 g) is added and the reaction is heated to 60° for 5 hours. Water (200 ml) is added and the solution is extracted with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and evaporated to yield 5-[2-(p-[ethoxycarbonylmethoxy]phenyl)ethen-1-yl]imidazo[1,5-a]pyridine.

Workup

  1. additionis added
  2. temperaturethe reaction is heated to 60° for 5 hours
  3. extractionthe solution is extracted with ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-c6101cfb69cd4263aba46af87fd668f3
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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