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

HRID 1192690
ノート
印刷プレビュー

反応式

HRID 1192690 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 583685787-Acetyl-5-fluoroquinolin-8-yl trifluoromethanesulfonateHCID 178505804HCID 178505804、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7c6bdce6a9c24b05ab3179c2ea46b5e6
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680108B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート