Chloroacetaldehyde → Methyl imidazo[1,2-a]pyridine-8-carboxylate

HRID 1473884Notes

Reaction equation

HRID 1473884 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].Cl[CH2:18][CH:19]=O.O>C(O)C>[N:1]1[CH:18]=[CH:19][N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]=12

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 962WaterHCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 15098894Methyl imidazo[1,2-a]pyridine-8-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 2-amino-pyridine-3-carboxylate (5 g, 35 mmol, 1.0 eq) in ethanol (250 mL) was added NaHCO3 (5.08 g) and chloroacetaldehyde in water (35 mL of 45% in water, 148 mmol, 4.5 eq). The reaction mixture was heated at reflux for 18 h. Solvent was removed and the residue was basified with Na2CO3 and then extracted with DCM. Organic layers were combined and evaporated to give a residue, which was purified by column to give the titled compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. customSolvent was removed
  4. extractionextracted with DCM
  5. customevaporated
  6. customto give a residue, which
  7. customwas purified by column

Sources & evidence

ORD record
ord-5bc479ae04964dce931ac259cdad4a14
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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