Triethylamine → Ethyl 5-hydroxypyridine-2-carboxylate

HRID 230774

Reaction equation

HRID 230774 reaction equation
C(N(CC)CC)C.Cl[C:9]1[N:14]=[CH:13][C:12]([OH:15])=[CH:11][CH: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]>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([C:24]([O:20][CH2:18][CH3:19])=[O:25])=[N:14][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8198212-Chloro-5-hydroxypyridineHCID 19794673N,N-dimethylformamide ethanolHCID 178418416HCID 178418416, compound

Product 1

HCID 23145820Ethyl 5-hydroxypyridine-2-carboxylate

Reagents, catalysts & solvents 2

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

Procedure

Palladium acetate (267 mg), 1,1′-bis(diphenylphosphino)ferrocene (1.3 g) and triethylamine (3.2 mL) were added to an ethanol-DMF mixed solvent (1/1, 20 mL) of 6-chloropyridin-3-ol (1.5 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 chloroform/methanol (10/1). 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=2/3) to obtain the entitled compound (500 mg).

Workup

  1. customEthanol was evaporated off under reduced pressure from the reaction solution, water
  2. additionwas added to the resulting residue
  3. extractionextracted with chloroform/methanol (10/1)
  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=2/3)

Sources & evidence

ORD record
ord-54ca4460d27647448c9b4774d48e1acd
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Linked notes

Loading…