Potassium Carbonate → HCID 57821730, compound

HRID 930340Notes

Reaction equation

HRID 930340 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.Br[CH:10]1[CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 57821730HCID 57821730, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 2-bromo-5-hydroxypyridine (1 g, 5.75 mmol), bromocyclobutane (0.783 mL, 8.33 mmol) and potassium carbonate (1.589 g, 11.49 mmol) in DMF (11.5 mL) was stirred at 60° C. for 5 h, then at 80° C. for 14 h. The reaction mixture was diluted with EtOAc and washed with water, saturated NaHCO3, and brine. The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by ISCO (40 g), eluting with a gradient of EtOAc/hexane 0-10% to provide to give 2-bromo-5-cyclobutoxypyridine (0.916 g, 4.02 mmol, 69.9% yield) as white solid. MS: M+ 228, 230. C9H10BrNO, MW=228.09

Workup

  1. waitat 80° C. for 14 h
  2. washwashed with water, saturated NaHCO3, and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by ISCO (40 g)
  6. washeluting with a gradient of EtOAc/hexane 0-10%
  7. customto provide

Sources & evidence

ORD record
ord-53afde1c2ec7414aa837a57a0c0d6fe0
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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