Water → HCID 23362919, compound

HRID 1081736Notes

Reaction equation

HRID 1081736 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.[H-].[Na+].[CH3:17]I.O>O1CCCC1>[CH3:17][O:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 233628905-[3-(Hydroxy)propylthio]imidazo[1,2-a]pyridine

Product 1

HCID 23362919HCID 23362919, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (803 mg, 3.86 mmoles) in tetrahydrofuran (30 ml) was added 60% sodium hydride in oil (0.19 g, 4.6 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 30 minutes. To the reaction mixture was added methyl iodide (0.36 ml, 5.8 mmoles), followed by stirring at room temperature overnight. The reaction mixture was poured into water, which was extracted with methylene chloride (30 ml×3). The methylene chloride layers were combined and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent:ethyl acetate) to obtain 308 mg of the desired product (35.9%, light brown oily product).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred under ice-
  3. temperaturecooling for 30 minutes
  4. stirringby stirring at room temperature overnight
  5. extractionwas extracted with methylene chloride (30 ml×3)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe residue was purified by column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-17083d6b5c3041e3a38c3e146cabe642
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

Loading…