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7-Acetyl-5-fluoroquinolin-8-yl trifluoromethanesulfonate → 1-[5-Fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanone

HRID 1192690
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HRID 1192690 반응식
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([F: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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:17][C:10]1[CH:9]=[C:8]([C:18](=[O:20])[CH3:19])[C:7]([C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([F:23])[CH:29]=2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2
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참가 물질

5

반응물 2

HCID 583685787-Acetyl-5-fluoroquinolin-8-yl trifluoromethanesulfonateHCID 178505804HCID 178505804, 화합물

생성물 1

HCID 583684731-[5-Fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanone수율 11%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

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온도
65 °C

실험 절차

A mixture of 7-acetyl-5-fluoroquinolin-8-yl trifluoromethanesulfonate (3.4 g, 10. mmol, from Example 53, Step 2) in tetrahydrofuran (10 mL) was degassed for 10 minutes, to which was added tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.0 mmol) and 0.5 M (3-fluorophenyl)(iodo)zinc in tetrahydrofuran (50 mL). The reaction mixture was heated at 65° C. overnight, and then cooled to room temperature. The reaction was quenched with sat. NaHCO3 solution. The mixture was filtered through a Celite pad. The filtrate was extracted with dichloromethane. The combined organic layers were wash with brine, dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 30% ethyl acetate in hexane) to give the desired product (0.32 g, 11%). LCMS calculated for C17H12F2NO (M+H)+: m/z=284.1; Found: 284.1.

후처리

  1. customwas degassed for 10 minutes, to which
  2. temperaturecooled to room temperature
  3. customThe reaction was quenched with sat. NaHCO3 solution
  4. filtrationThe mixture was filtered through a Celite pad
  5. extractionThe filtrate was extracted with dichloromethane
  6. washThe combined organic layers were wash with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. custompurified on silica gel (eluting with 0 to 30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-7c6bdce6a9c24b05ab3179c2ea46b5e6
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680108B2

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