HCID 67247801, compound → HCID 67254163, compound

HRID 1190862Notes

Reaction equation

HRID 1190862 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[N:9]2)[CH:3]=1>COCCOC.C(OCC)(=O)C.O.[Fe].[Fe](Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[CH:8]=[C:4]2[CH:3]=1

Participants

7

Reactant 1

HCID 67247801HCID 67247801, compound

Product 1

HCID 67254163HCID 67254163, compound

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 24458Ferrous ChlorideCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.746 g of 4-bromo-2-(3-p-tolyl-2H-azirin-2-yl)pyridine obtained in step 13.2 is dissolved in the presence of 6.6 mg (0.052 mmol) of iron (H) chloride in 30 mL of 1,2-dimethoxyethane. The medium is then refluxed for 6 hours. A further 10 mg (0.078 mmol) of iron (II) chloride are then added and the mixture is refluxed again with stirring for 3 hours. The medium is then diluted with 50 mL of ethyl acetate and 50 mL of water. The organic phase is then recovered, dried over sodium sulfate and filtered. 2 g of silica are then added to the filtrate, followed by concentrating under reduced pressure. The powder obtained is used as a solid deposit for a chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (85/15). 0.534 g (71%) of expected compound is recovered in the faun of a yellow powder.

Workup

  1. temperatureThe medium is then refluxed for 6 hours
  2. temperaturethe mixture is refluxed again
  3. customThe organic phase is then recovered
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. addition2 g of silica are then added to the filtrate
  7. concentrationby concentrating under reduced pressure
  8. customThe powder obtained
  9. washeluting with a mixture of cyclohexane and ethyl acetate (85/15)
  10. custom0.534 g (71%) of expected compound is recovered in the faun of a yellow powder

Sources & evidence

ORD record
ord-0795101c4d504643a5cde64190a5cefe
Source dataset
uspto-grants-2014_03
Patent number
US08680096B2

Reaction notes

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