Acetonitrile → HCID 86670587, compound

HRID 401448Notes

Reaction equation

HRID 401448 reaction equation
BrC(C=O)C=O.Br[C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([CH:17]=[O:18])=[CH:15][N:16]=2)[CH:13]=1.Br[C:20]1[CH:21]=[CH:22][C:23](N)=[N:24][CH:25]=1.C(#N)C>>[N:24]1[CH:25]=[CH:20][CH:21]=[C:22]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH:17]=[O:18])=[CH:15][N:16]=3)[CH:13]=2)[CH:23]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 706222-Amino-5-bromopyridineHCID 86670588HCID 86670588, compound

Product 1

HCID 86670587HCID 86670587, compoundYield 53%

Procedure

6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde Bromomalonaldehyde (5230 mg, 34.68 mmol) was added to a solution of 5-bromopyridin-2-amine in acetonitrile (5000 mg, 28.90 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 EtOAc. The organic layer was washed with brine and dried over sodium sulfate. The organic layer was concentrated in vacuo and the product was purified by column chromatography using EtOAc-petroleum ether gradient to obtain the title compound. Yield: 53%; 1H NMR (DMSO-d6; 300 MHz): δ 9.94 (s, 1H), 9.50 (s, 1H), 8.54 (s, 1H), 7.86-7.85 (m, 2H); MS (m/z): 226 (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 EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe organic layer was concentrated in vacuo
  8. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-0ae02b2b0e3b45c7a2831ca9473fecd8
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Reaction notes

Loading…