Acetonitrile → 6-Bromo-7-methylimidazo[1,2-a]pyridine-3-carbaldehyde

HRID 401450

Reaction equation

HRID 401450 reaction equation
Br[CH:2]([CH:5]=[O:6])[CH:3]=O.[Br:7][C:8]1[C:9]([CH3:15])=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.C(#N)C>>[Br:7][C:8]1[C:9]([CH3:15])=[CH:10][C:11]2[N:12]([C:2]([CH:5]=[O:6])=[CH:3][N:14]=2)[CH:13]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 749452-BromopropanedialHCID 8176952-Amino-5-bromo-4-methylpyridine

Product 1

HCID 467391706-Bromo-7-methylimidazo[1,2-a]pyridine-3-carbaldehydeYield 79.81%

Procedure

Bromomalonaldehyde (5000 mg, 26.74 mmol) was added to a solution of 5-bromo-4-methylpyridin-2-amine in acetonitrile (5250 mg, 34.76 mmol). The reaction mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was quenched with sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The organic layer was concentrated in vacuum and the product was purified by column chromatography using ethyl acetate-petroleum ether gradient to obtain the title compound. Yield: 79.81%; 1H NMR (DMSO-d6; 300 MHz): δ 9.90 (s, 1H), 9.52 (s, 1H), 8.51 (s, 1H), 7.94 (s, 1H), 2.50 (s, 3H); MS (m/z): 239 (M+1)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. customAfter completion of the reaction
  3. customthe reaction mixture was quenched with sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe organic layer was concentrated in vacuum
  8. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-6d8c8ba4621b4fc49b9ec3657cfabb8b
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Linked notes

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