Dimethylformamide → HCID 66520836, compound

HRID 1620084Notes

Reaction equation

HRID 1620084 reaction equation
[N:1]1(O)C=[CH:5][CH:4]=[CH:3][CH2:2]1.[C:8](=[O:11])([O-])[O-].[Cs+].[Cs+].CN(C=O)C.Br[C:20]1[CH:21]=[N:22][CH:23]=[C:24]([Br:26])[CH:25]=1>[Cu](I)I.O>[Br:26][C:24]1[CH:25]=[C:20]([N:1]2[CH:2]=[CH:3][CH:4]=[CH:5][C:8]2=[O:11])[CH:21]=[N:22][CH:23]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 693693,5-DibromopyridineHCID 21882869HCID 21882869, compound

Product 1

HCID 66520836HCID 66520836, compoundYield 12.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Pyridin-1-ol (96 mg), cesium carbonate (412 mg), and copper iodide (50 mg) were added to a tube containing a DMF (4 ml) solution containing 3,5-dibromopyridine (200 mg) and the tube was sealed in a nitrogen atmosphere, followed by stirring at 120° C. for 11 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:5 to 1:1), and a brown solid of 5′-bromo-2H-[1,3′-bipyridine]-2-one (25.8 mg) was thus obtained.

Workup

  1. customthe tube was sealed in a nitrogen atmosphere
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:5 to 1:1)

Sources & evidence

ORD record
ord-c4b727c09f3e47b795ae30ea8ef9ef22
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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