2-Amino-4-bromopyridine-3-carbonitrile → 7-Bromo-3-(2,2,2-trifluoro-ethyl)-imidazo[1,2-a]pyridine-8-carbonitrile

HRID 2361744Notes

Reaction equation

HRID 2361744 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[C:4]#[N:5].Br[CH:12]([CH2:15][C:16]([F:19])([F:18])[F:17])[CH:13]=O>CCO.CCOC(C)=O>[Br:10][C:6]1[CH:7]=[CH:8][N:9]2[C:12]([CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:13][N:1]=[C:2]2[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 580811212-Amino-4-bromopyridine-3-carbonitrileHCID 580811402-Bromo-4,4,4-trifluorobutyraldehyde

Product 1

HCID 580811287-Bromo-3-(2,2,2-trifluoro-ethyl)-imidazo[1,2-a]pyridine-8-carbonitrileYield 48.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of compounds D8 (2 g, 10.1 mmol) and D4 (2.898 g, 14.14 mmol) in EtOH (10 ml) was subjected to microwave heating at 150° C. for 40 min. After cooling to room temperature, the solvent was evaporated in vacuo. The residue thus obtained was diluted with EtOAc and washed with water. The organic layer was separated and washed with water, then with 1M HCl (aqueous solution), dried (MgSO4) and evaporated in vacuo. The crude product thus obtained was triturated with diethylether to yield compound D9 (1.5 g, 48.8%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated in vacuo
  3. customThe residue thus obtained
  4. washwashed with water
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialwith 1M HCl (aqueous solution), dried (MgSO4)
  8. customevaporated in vacuo
  9. customThe crude product thus obtained
  10. customwas triturated with diethylether

Sources & evidence

ORD record
ord-4f1da4511e3c44189c88ec8c78263079
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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