Water → HCID 57791289, compound

HRID 249727Notes

Reaction equation

HRID 249727 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:11])=[N:6][C:7]([CH3:10])=[CH:8][CH:9]=1)[CH3:2].[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:10][C:7]1[N:6]=[C:5]([F:11])[C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 57791309HCID 57791309, compound

Product 1

HCID 57791289HCID 57791289, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Ethoxy-2-fluoro-6-methylpyridine (400 mg) was initially introduced in carbon tetrachloride (30 ml) and, after addition of N-bromosuccinimide (505 mg) and 2,2′-azobis(2-methylpropionitrile) (85 mg), the reaction mixture was heated at reflux for 7 h. After standing overnight at RT, it was treated with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (n-heptane-ethyl acetate gradient). After the combination of the product-containing fractions, it was brought to dryness. 393 mg of the desired compound were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 7 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (n-heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-03517d09f06242d69afc61f8270e78d2
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

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