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7-Acetyl-5-methylquinolin-8-yl trifluoromethanesulfonate → 1-[8-(3-Fluorophenyl)-5-methylquinolin-7-yl]ethanone

HRID 1192561
Notes
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Reaction equation

HRID 1192561 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([CH3:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[F:23][C:24]1[CH:25]=[C:26]([Zn]I)[CH:27]=[CH:28][CH:29]=1>O1CCCC1>[F:23][C:24]1[CH:29]=[C:28]([C:7]2[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([CH3:17])=[C:11]3[C:16]=2[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:27]=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 583684117-Acetyl-5-methylquinolin-8-yl trifluoromethanesulfonateHCID 178505804HCID 178505804, compound

Product 1

HCID 583686621-[8-(3-Fluorophenyl)-5-methylquinolin-7-yl]ethanoneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a mixture of 7-acetyl-5-methylquinolin-8-yl trifluoromethanesulfonate (0.833 g, 2.50 mmol) in tetrahydrofuran (20 mL), with stirring, was added 0.5 M (3-fluorophenyl)(iodo)zinc in THF (10.0 mL, 5.0 mmol), followed by tetrahydrofurantetrakis(triphenylphosphine)palladium(0) (289 mg, 0.250 mmol). The reaction mixture was heated at 60° C. overnight, cooled to room temperature and quenched with sat. sodium bicarbonate. The mixture was filtered through a Celite pad. The filtrate was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated under reduced pressure. The residue was purified on silica gel, eluting with 0 to 80% ethyl acetate in hexane, to give the desired product (0.379 g, 54%). LCMS calculated for C18H14FNO (M+H)+: m/z=280.1; Found: 280.0.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with sat. sodium bicarbonate
  3. filtrationThe mixture was filtered through a Celite pad
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified on silica gel
  9. washeluting with 0 to 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b9deb54eb05a4b2c9bd0be7fc3704985
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680108B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes