Sodium hydride → HCID 58355757, compound

HRID 1184061Notes

Reaction equation

HRID 1184061 reaction equation
[OH:1][CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].[CH3:18][O:19][CH2:20][CH2:21]Br>CN(C=O)C>[CH3:18][O:19][CH2:20][CH2:21][O:1][CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 10488485HCID 10488485, compound

Product 1

HCID 58355757HCID 58355757, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-2-carboxylate (0.30 g) in DMF (5 ml) was added sodium hydride (60 mg) under ice-cooling. The mixture was stirred at room temperature for 30 min, 2-methoxyethyl bromide (220 mg) was added under ice-cooling, and the mixture was stirred at 60° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with aqueous potassium carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (0:10-10:0) was concentrated under reduced pressure to give the object product (0.16 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at 60° C. for 3 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionthe residue was diluted with aqueous potassium carbonate
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. washa fraction eluted with ethyl acetate-hexane (0:10-10:0)
  11. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-4219e8cde2574552bd833b403be36b47
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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