Lithium acetate → Methyl 2-(quinolin-5-yl)propanoate

HRID 1814305Notes

Reaction equation

HRID 1814305 reaction equation
C([O-])(=O)C.[Li+].FC(F)(F)S(O[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2)(=O)=O.[CH3:24][O:25]/[C:26](/[O:29][Si](C)(C)C)=[CH:27]\[CH3:28]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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]>[N:17]1[C:18]2[C:13](=[C:12]([CH:27]([CH3:28])[C:26]([O:25][CH3:24])=[O:29])[CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 3474584Lithium acetateHCID 108557751-Methoxy-1-trimethylsilyloxypropeneHCID 114714035-Quinolyl trifluoromethanesulfonate

Product 1

HCID 22504014Methyl 2-(quinolin-5-yl)propanoate

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tris(dibenzylideneacetone)-dipalladium (65 mg, 0.14 mmol), 1,1′-bis(diphenylphosphino)ferrocene(155 mg, 0.28 mmol) and lithium acetate(2.8 g, 27.6 mmol) in THF (50 mL) was stirred at room temperature for 5 minutes. To this mixture was added 5-quinolyl trifluoromethanesulfonate and [(E)-1-methoxy-1-propenyl]oxy(trimethyl)silane. The resulting mixture was heated at reflux for 24 hours and then allowed to cool to room temperature. The mixture was filtered, the residue was washed with THF(50 mL) and the solvent was removed under reduced pressure. Following a short silica column and aqueous workup, methyl 2-(5-quinolyl)propanoate was purified by HPLC yield 250 mg, 17%. HPLC (10% to 90% acetonitrile in 0.1N aqueous ammonium acetate over 10 min at 2 mL/min using a Waters Symmetry C18, 150×4.6 mm column) 6.89 min.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe mixture was filtered
  4. washthe residue was washed with THF(50 mL)
  5. customthe solvent was removed under reduced pressure
  6. customwas purified by HPLC yield 250 mg, 17%
  7. custom6.89 min.

Sources & evidence

ORD record
ord-3c9fd161dd6f4cecb9d05c0c59617e0f
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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