Water → HCID 4678178, compound

HRID 1896447Notes

Reaction equation

HRID 1896447 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[C:12]=1[CH:13]=[O:14].O>CCO>[Cl:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[C:12]=1[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 962WaterHCID 20641342-Chloroimidazo[1,2-a]pyridine-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 4678178HCID 4678178, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (1.52 g, 41.33 mmol, 1.5 eq) is added to a solution of 2-chloroimidazo[1,2-a]pyridine-3-carbaldehyde x173 (4.96 g, 27.56 mmol, 1 eq) in EtOH (100 ml). After 1 hour at room temperature, water (100 ml) is added and the aqueous layer is extracted with CH2Cl2 (3×50 ml). The combined organic layers are dried on anhydrous MgSO4, filtered and evaporated under reduced pressure. The resulting white solid is recrystallized in CH2Cl2/hexane to yield 3.9 g of (2-chloroimidazo[1,2-a]pyridin-3-yl)methanol x174.

Workup

  1. extractionthe aqueous layer is extracted with CH2Cl2 (3×50 ml)
  2. dry with materialThe combined organic layers are dried on anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe resulting white solid is recrystallized in CH2Cl2/hexane

Sources & evidence

ORD record
ord-08cd53d9a6a246f292dffed06824a941
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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