Water → Imidazo[1,2-a]pyridin-6-ylmethanol

HRID 1757106Notes

Reaction equation

HRID 1757106 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:5]=12.[BH4-].[Na+].O.ClCCl.CO>CO>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 7164582Imidazo[1,2-a]pyridine-6-carbaldehydeHCID 21226129Dichloromethane methanol

Product 1

HCID 7060530Imidazo[1,2-a]pyridin-6-ylmethanolYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.90 g of the 6-imidazo[1,2-a]pyridinecarbaldehyde prepared in the Preparative Example 5 was dissolved in 20 ml of methanol. The obtained solution was stirred under cooling with ice, followed by the addition of 90 mg of sodium borohydride. The obtained mixture was stirred for 50 minutes, followed by the addition of water. The obtained mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (30:1 to 10:1) to give 0.52 g of the title compound as a faintly orange-yellow solid (yield: 57%).

Workup

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred for 50 minutes
  3. extractionThe obtained mixture was extracted with chloroform
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe obtained residue was purified by silica gel column chromatography [solvent

Sources & evidence

ORD record
ord-3eb3d60176fb4899ad4971a677c4776e
Source dataset
uspto-grants-1995_08
Patent number
US05444066

Reaction notes

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