Potassium Carbonate → 1160790-03-3

HRID 2068680Notes

Reaction equation

HRID 2068680 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].BrC[CH2:17][CH2:18][O:19][CH2:20]CCBr>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:17][CH2:18][O:19][CH3:20])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5995285-Bromo-2-hydroxypyridineHCID 112307051-Bromo-3-(3-bromopropoxy)propane

Product 1

HCID 606986761160790-03-3Yield 75.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-2(1H)-pyridone (0.10 g, 0.57 mmol) in acetone (5.0 ml) was added K2CO3 (0.18 g, 2.60 mmol followed by addition of 2-bromo-ethyl-methylether (0.24 g, 1.70 mmol). The resulting reaction mixture was heated to 60° C. for 16 h. After the completion of reaction (TLC monitoring), acetone was distilled off, added water and extracted with DCM (3×10 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (60-120 M, 1% MeOH-DCM) to obtain the desired product (0.10 g, 75%). MS: 232.01 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. distillationwas distilled off
  3. additionadded water
  4. extractionextracted with DCM (3×10 mL)
  5. washThe combined organics was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified over silica gel (60-120 M, 1% MeOH-DCM)

Sources & evidence

ORD record
ord-f66bc8bd6ec247fa84a6a387bb7a5ee9
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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