Dimethylformamide → HCID 68702328, compound

HRID 723528Notes

Reaction equation

HRID 723528 reaction equation
[N+:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](=O)([O-])[O-].[K+].[K+].BrC[C:16]([O:18][CH3:19])=[O:17].CN([CH:23]=[O:24])C>>[CH3:19][O:18][C:16]([CH2:23][O:24][C:5]1[CH:4]=[CH:3][C:2]([CH3:8])=[N+:1]([O-:7])[CH:6]=1)=[O:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12753Pyridine N-OxideHCID 60984Methyl bromoacetate

Product 1

HCID 68702328HCID 68702328, compound

Procedure

A solution of the pyridine N-oxide (309a) (21.12 g) in DMF (450 ml) was treated with potassium carbonate (26.2 g) and, after 30 mins., with methyl bromoacetate (16 ml), and stirred overnight. Solvent was evaporated, saturated brine (500 ml) added and the mixture extracted with chloroform (6×200 ml). The combined organic solution was dried and evaporated and the residue chromatographed (20% EtOH in EtOAc) to give product (18.5 g).

Workup

  1. customSolvent was evaporated
  2. additionsaturated brine (500 ml) added
  3. extractionthe mixture extracted with chloroform (6×200 ml)
  4. customThe combined organic solution was dried
  5. customevaporated
  6. customthe residue chromatographed (20% EtOH in EtOAc)

Sources & evidence

ORD record
ord-388e07c44adc48c5a6150ad04478648f
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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