Potassium Carbonate → 5-Bromo-2-(cyclopropylmethoxy)-3-fluoropyridine

HRID 2277156Notes

Reaction equation

HRID 2277156 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]([OH:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH:18]1[CH2:20][CH2:19]1>CN(C=O)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]([O:8][CH2:17][CH:18]2[CH2:20][CH2:19]2)=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 1785175945-Bromo-3-fluoro-1,2-dihydropyridin-2-one

Product 1

HCID 867151175-Bromo-2-(cyclopropylmethoxy)-3-fluoropyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromo-3-fluoropyridin-2-ol (1.00 g) in DMF (10 mL) were added potassium carbonate (1.44 g) and (bromomethyl)cyclopropane (0.758 mL), and the mixture was stirred with heating at 70° C. for 30 min. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate and water, and the organic layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (491 mg).

Workup

  1. temperatureto cool to room temperature
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5f731484d9ca4b23a1c92c7461d5a90a
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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