Hydrochloric Acid → HCID 59589379, compound

HRID 630180Notes

Reaction equation

HRID 630180 reaction equation
Br[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([Cl:13])[CH:5]=[CH:4][N:3]=1.[CH:14]([Zn]C(C)C)([CH3:16])[CH3:15].O.Cl>O1CCOCC1>[Cl:13][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH:14]([CH3:16])[CH3:15])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 59589350Ethyl 2-bromo-4-chloronicotinateHCID 178461828HCID 178461828, compound

Product 1

HCID 59589379HCID 59589379, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 2-bromo-4-chloropyridine-3-carboxylate (1 g, 3.78 mmol) was dissolved in anhydrous dioxane (30 mL). A solution of diisopropyl zinc (4.5 mL, 4.54 mmol, 1.0 M in toluene) was added dropwise, followed with (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (44 mg, 60 μmol). The mixture was heated at 40° C. overnight, and water followed with 1 N HCl was added. The reaction 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 0-15% hexane/ethyl acetate to afford ethyl 4-chloro-2-(propan-2-yl)pyridine-3-carboxylate (428 mg, 50% yield).

Workup

  1. additionwas added
  2. extractionThe reaction 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 0-15% hexane/ethyl acetate

Sources & evidence

ORD record
ord-ce5974a9bf5840769966a9465a2b7765
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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