Chloroacetaldehyde → Imidazo[1,2-a]pyridine-7-methanol

HRID 341196

Reaction equation

HRID 341196 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].Cl[CH2:16][CH:17]=O>CCO>[N:1]1[CH:16]=[CH:17][N:3]2[CH:4]=[CH:5][C:6]([CH2:8][OH:9])=[CH:7][C:2]=12

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 1515296(2-Aminopyridin-4-yl)methanol

Product 1

HCID 11051824Imidazo[1,2-a]pyridine-7-methanolYield 81.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2-amino-pyridin-4-yl)-methanol (0.40 g, 3.3 mmol) in EtOH was added NaHCO3 (0.56 g, 6.67 mmol) followed by chloroacetaldehyde (0.81 ml, 5.0 mmol). The mixture was refluxed for 2 h. Solvents were removed in vacuo and the crude mixture was partitioned between water and EtOAc. The aqueous was further extracted with EtOAc, the organics combined, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using silica column chromatography (0-50% MeOH/Et2O) to afford 0.40 g of product MS: [M+H]+=149.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customSolvents were removed in vacuo
  3. customthe crude mixture was partitioned between water and EtOAc
  4. extractionThe aqueous was further extracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-b27409053b5d4770aa2cfe90e0ddea18
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Linked notes

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