2-Bromopropanedial → 6-Bromo-5-methylimidazo[1,2-a]pyridine-3-carbaldehyde

HRID 401453

Reaction equation

HRID 401453 reaction equation
Br[CH:2]([CH:5]=[O:6])[CH:3]=O.[Br:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:15])=[N:12][C:13]=1[CH3:14]>C(#N)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:2]([CH:5]=[O:6])=[CH:3][N:15]=2)[C:13]=1[CH3:14]

Participants

4

Reactant 2

HCID 749452-BromopropanedialHCID 1706782-Pyridinamine, 5-bromo-6-methyl-

Product 1

HCID 866706016-Bromo-5-methylimidazo[1,2-a]pyridine-3-carbaldehydeYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromomalonaldehyde (464 mg, 3.07 mmol) was added to a solution of 5-bromo-6-methylpyridin-2-amine (500 mg, 2.67 mmol) in acetonitrile. The reaction mixture was refluxed for 1 hour. 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 and the product was purified by column chromatography using up to 0.5% methanol in chloroform gradient to obtain the title compound. Yield: 28%; 1H NMR (DMSO-d6; 300 MHz): δ 10.06 (s, 1H), 8.51 (s, 1H), 7.86-7.83 (d, 1H, J=9.3 Hz), 7.68 (d, 1H, J=9.3 Hz), 3.03 (s, 3H); MS: m/z 240.1 (M+1)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  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
  8. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-f4ced2759f824b10b985a54b42069db9
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Linked notes

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