Piperidine → HCID 58521863, 화합물

HRID 2390122노트

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HRID 2390122 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])[CH:3]=1.[C:14]([O:18][C:19](=[O:31])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[C:29]#[CH:30])([CH3:17])([CH3:16])[CH3:15].N1CCCCC1>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:14]([O:18][C:19](=[O:31])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[C:29]#[C:30][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH2:11][CH2:12][CH3:13])(=[O:10])=[O:9])[CH:3]=1)([CH3:17])([CH3:16])[CH3:15]

참가 물질

6

반응물 3

HCID 8082PiperidineHCID 565942651-Bromo-3-(propylsulfonyl)benzene2회HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2회

생성물 1

HCID 58521863HCID 58521863, 화합물

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

A mixture of 1-bromo-3-(propane-1-sulfonyl)-benzene (Intermediate 5; 493 mg, 1.87 mmol), tert-butyl(4-chloro-2-ethynylphenoxy)acetate (Intermediate 3, 500 mg; 1.87 mmol), dichlorobis(triphenylphosphine)palladium(II) (52 mg; 0.07 mmol) and piperidine (550 μL; 5.6 mmol) was heated at 70° C. for 18 hours. The reaction mixture was taken up in EtOAc, washed twice with citric acid (0.5 M aqueous solution) and once with brine. The organic phase was dried over MgSO4, filtered and concentrated to dryness affording a crude, which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc. The title compound was obtained as a dark orange sticky solid (640 mg, 76%).

후처리

  1. washwashed twice with citric acid (0.5 M aqueous solution) and once with brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customaffording a crude, which
  6. customwas purified by flash column chromatography (silica)
  7. washeluting with cyclohexane containing
  8. temperatureincreasing amounts of EtOAc

출처 및 근거

ORD 기록
ord-54a81745d2d14279b9ac310038afb5ee
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273769B2

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