Chloroform → Imidazo(1,5-a)pyridine

HRID 1926499Notes

Reaction equation

HRID 1926499 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH:9](Cl)(Cl)Cl.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.COCCOC>[CH:2]1[N:1]=[CH:9][N:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=12

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 195092-Pyridinemethanamine

Product 1

HCID 274090Imidazo(1,5-a)pyridineYield 16.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a flask were added 2.0 g of 2-(aminomethyl)pyridine, 0.12 g of tetrabutylammonium bromide, 5.7 g of chloroform, and 30 ml 1,2-dimethoxyethane. While stirring under nitrogen, 40 ml of 40% aqueous Sodium hydroxide was added and the mixture was heated to 50 C for 4.5 hours. After cooling to 22 C, the mixture was extracted twice with ethyl acetate, and the ethyl acetate layer was dried over sodium sulfate. After filtration and solvent removal, the product was purified by silica gel chromatography using straight ethyl acetate to 5% acetonitrile in ethyl acetate resulting in a brown oil which crystallized on standing. The product was sublimed to give 0.36 g of a yellow solid.

Workup

  1. temperaturethe mixture was heated to 50 C for 4.5 hours
  2. temperatureAfter cooling to 22 C
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. dry with materialthe ethyl acetate layer was dried over sodium sulfate
  5. filtrationAfter filtration and solvent removal
  6. customthe product was purified by silica gel chromatography
  7. customcrystallized

Sources & evidence

ORD record
ord-b896b6a91ef549b5baaa232df5d0f307
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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