Potassium Carbonate → 3-Bromo-5-(2-methoxyethoxy)pyridine

HRID 445607Notes

Reaction equation

HRID 445607 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][CH2:17][CH2:18]Br>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:18][CH2:17][O:16][CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 107759113-Bromo-5-(2-methoxyethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-5-hydroxypyridine (Aldrich, Buchs, Switzerland, 611 mg, 3.51 mmol), potassium carbonate (971 mg, 7.02 mmol) and 2-bromoethyl methyl ether (537 mg, 3.86 mmol) in 30 ml DMF was stirred for 14 h at rt and for 2 h at 80° C. The reaction mixture was quenched with water and extracted with EtOAc (2×). The organic layers were washed with brine (3×), dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (dichloromethane/MeOH 0% to 3%) to give the title compound as an oil. (HPLC: tR 2.38 min (Method A); M+H=232, 234 MS-ES).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layers were washed with brine (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (dichloromethane/MeOH 0% to 3%)

Sources & evidence

ORD record
ord-c747b2d5308d40f3beabc404f238ef07
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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