Potassium Carbonate → HCID 57821730, compound

HRID 707376Notes

Reaction equation

HRID 707376 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 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-5-hydroxypyridine (1.0 g, 5.75 mmol), bromocyclobutane (0.783 mL, 8.33 mmol), and potassium carbonate (1.59 g, 11.5 mmol) were mixed in DMF (11 mL) and 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 (0.92 g, 4.0 mmol, 70% yield) as white solid. ESI (M+1) 229.9.

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-f04663bcf11b4966b802917d5e3dbc8f
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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