Bromine → HCID 18182373, compound

HRID 1359270Notes

Reaction equation

HRID 1359270 reaction equation
[Br:1]Br.[CH2:3]([C:10]1[C:11]([O:16][CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+]>CO>[CH2:3]([C:10]1[C:11]([O:16][CH3:17])=[N:12][CH:13]=[C:14]([Br:1])[CH:15]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 18182300HCID 18182300, compound

Product 1

HCID 18182373HCID 18182373, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.12 ml of bromine was added to a mixture of 430 mg of 3-benzyl-2-methoxypyridine, 460 mg of sodium bicarbonate and 10 ml of methanol under stirring in an ice bath, followed by stirring at room temperature for 8 hours. The mixture was partitioned by adding an aqueous sodium thiosulfate solution and ethyl acetate thereto. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography and eluted with 5% ethyl acetate/hexane, to give 140 mg of the target compound.

Workup

  1. stirringby stirring at room temperature for 8 hours
  2. customThe mixture was partitioned
  3. additionby adding an aqueous sodium thiosulfate solution and ethyl acetate
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-894034b25bca49d4a8f7d10e9d3e152e
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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