Chloroacetaldehyde → HCID 67458178, compound

HRID 2389289Notes

Reaction equation

HRID 2389289 reaction equation
[NH2:1][C:2]1[C:13]([Br:14])=[CH:12][C:5]([C:6]([N:8]([CH2:10][CH3:11])[CH3:9])=[O:7])=[CH:4][N:3]=1.Cl[CH2:16][CH:17]=O.C(=O)([O-])O.[Na+]>C(O)C>[Br:14][C:13]1[C:2]2[N:3]([CH:16]=[CH:17][N:1]=2)[CH:4]=[C:5]([C:6]([N:8]([CH2:10][CH3:11])[CH3:9])=[O:7])[CH:12]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 67453699HCID 67453699, compound

Product 1

HCID 67458178HCID 67458178, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Amino-5-bromo-N-ethyl-N-methylnicotinamide (250 mg, 0.97 mmol) obtained in Step 1 of Example 170 was dissolved in ethanol (2.5 mL), and a 50% aqueous chloroacetaldehyde solution was added thereto, and the mixture was stirred overnight under reflux. After the mixture was left to cool to room temperature, an aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted with a chloroform/isopropanol (6/1) mixed solution. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=98/2) to give 8-bromo-N-ethyl-N-methylimidazo[1,2-a]pyridine-6-carboxamide (65 mg, 0.23 mmol, yield: 24%).

Workup

  1. temperatureunder reflux
  2. waitAfter the mixture was left
  3. extractionthe mixture was extracted with a chloroform/isopropanol (6/1)
  4. additionmixed solution
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform/methanol=98/2)

Sources & evidence

ORD record
ord-9a6ccf1b15d349b8840a1ac8123495d3
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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