Triethylamine → Ethyl 5-Chloropyridine-2-carboxylate

HRID 230771

Reaction equation

HRID 230771 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=1.[C]=O.[CH2:18]([OH:20])[CH3:19].CN([CH:24]=[O:25])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:24]([O:20][CH2:18][CH3:19])=[O:25])=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8170982-Bromo-5-chloropyridineHCID 19794673N,N-dimethylformamide ethanolHCID 178418416HCID 178418416, compound

Product 1

HCID 15414989Ethyl 5-Chloropyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Procedure

Palladium acetate (117 mg), 1,1′-bis(diphenylphosphino)ferrocene (577 mg) and triethylamine (1.4 mL) were added to an ethanol-DMF mixed solvent (1/1, 30 mL) of 2-bromo-5-chloropyridine (1.0 g), and stirred overnight in a carbon monoxide atmosphere (1 atmospheric pressure) at 50° C. Ethanol was evaporated off under reduced pressure from the reaction solution, water was added to the resulting residue, and extracted with hexane/ethyl acetate (2/3). The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 4/1) to obtain the entitled compound (1.4 g).

Workup

  1. customEthanol was evaporated off under reduced pressure from the reaction solution, water
  2. additionwas added to the resulting residue
  3. extractionextracted with hexane/ethyl acetate (2/3)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated off under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 4/1)

Sources & evidence

ORD record
ord-3357ba49289043cfb599c5ea7e8e0095
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Linked notes

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