Potassium Carbonate → HCID 18182263, compound

HRID 1359295Notes

Reaction equation

HRID 1359295 reaction equation
[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][CH:11]=[C:10]([OH:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][CH2:24][CH2:25]Br>CN(C)C=O>[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][CH:11]=[C:10]([O:15][CH2:25][CH2:24][O:23][CH3:22])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178515815HCID 178515815, compound

Product 1

HCID 18182263HCID 18182263, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5 g of 2-benzyl-3-bromo-6-hydroxypyridine, 3.9 g of anhydrous potassium carbonate, 2.7 ml of 2-bromoethyl methyl ether and 20 ml of N,N-dimethylformamide was heated under stirring in an oil bat kept at 80° C. for one hour. After cooling as it was, the mixture was extracted with ethyl acetate-water. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 1-3% ethyl acetate/hexane, to give 4.2 g of the target compound.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling as it
  3. extractionthe mixture was extracted with ethyl acetate-water
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. washeluted with 1-3% ethyl acetate/hexane

Sources & evidence

ORD record
ord-561e45f71247475fb996c2fdb2e8569b
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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