Potassium Carbonate → 2-Bromo-5-(cyclopropylmethoxy)pyridine

HRID 1888753Notes

Reaction equation

HRID 1888753 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH:17]1[CH2:19][CH2:18]1>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:16][CH:17]2[CH2:19][CH2:18]2)=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 578217962-Bromo-5-(cyclopropylmethoxy)pyridineYield 96.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-bromopyridin-3-ol (5.00 g, 28.8 mmol) in DMF (50 mL) were added potassium carbonate (7.96 g, 55.6 mmol) and (bromomethyl)cyclopropane (4.18 mL, 43.1 mmol), and the mixture was stirred at 60° C. for 30 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed three times with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 1:1) to give the title compound (6.32 g, yield 96%) as an oil.

Workup

  1. washthe mixture was washed three times with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 1:1)

Sources & evidence

ORD record
ord-89ef87a90f83479992b844794754357f
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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