Hydrochloric Acid → Ethyl 2,4-diethylpyridine-3-carboxylate

HRID 630192Notes

Reaction equation

HRID 630192 reaction equation
Br[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:14]([Zn]CC)[CH3:15].O.Cl.O1CCO[CH2:23][CH2:22]1>>[CH2:14]([C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH2:22][CH3:23])[CH:5]=[CH:4][N:3]=1)[CH3:15]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 59589350Ethyl 2-bromo-4-chloronicotinateHCID 178418750HCID 178418750, compound

Product 1

HCID 59589505Ethyl 2,4-diethylpyridine-3-carboxylateYield 46%

Conditions

Temperature
70 °C

Procedure

Ethyl 2-bromo-4-chloropyridine-3-carboxylate (2.0 g, 7.6 mmol) was dissolved in anhydrous dioxane (55 mL). A solution of diethyl zinc (6.9 mL, 7.6 mmol, 1.1 M in toluene) was added dropwise, and then was added (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (83 mg, 113 μmol). The mixture was heated at 70° C. for 6 hours, and water followed by 1 N HCl was added. The mixture was extracted 3 times with ethyl acetate, and the combined organic phases were washed with brine and dried over sodium sulfate. After evaporation, the residue was dissolved in DCM and purified on silica gel using 0-20% hexane/ethyl acetate to afford ethyl 2,4-diethylpyridine-3-carboxylate (720 mg, 46% yield).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted 3 times with ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation
  6. dissolutionthe residue was dissolved in DCM
  7. custompurified on silica gel using 0-20% hexane/ethyl acetate

Sources & evidence

ORD record
ord-cc541b2226a64e04bdd0c20aeb69ea6c
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…