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1H-Isoindole-1,3(2H)-dione, 2-ethenyl- → {2-[2-(1.3-Dioxo-1,3-dihydro-isoindol-2-yl)-vinyl]-phenyl}-acetic acid

HRID 480360
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인쇄 미리보기

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HRID 480360 반응식
C([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)(C)(C)C.[CH:16]([N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])=[CH2:17].C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[O:28]=[C:19]1[C:20]2[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:23])[N:18]1[CH:16]=[CH:17][C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:7][C:6]([OH:5])=[O:15]
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HCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 53936336Tert-butyl 2-(3-bromophenyl)acetate

생성물 1

HCID 73877575{2-[2-(1.3-Dioxo-1,3-dihydro-isoindol-2-yl)-vinyl]-phenyl}-acetic acid수율 30.5%

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

A mixture of 3-bromo-phenyl acetic acid tert-butyl ester (5.64 g, 20.80 mmol), N-vinyl phthalimide (3.60 g, 20.80 mmol), diisopropylethylamine (3.63 g, 28.08 mmol), palladium acetate (107 mg, 0.478 mmol), and tritolylphosphine (475 mg, 1.56 mmol) in acetonitrile (10 mL) was stirred at 90° C. for 20 h. The reaction was cooled to room temperature and ice water (50 mL) was added. EtOAc (50 mL) was added and the organic solution was washed with 5.5% HCl followed by brine. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 9:1 to 4:1) provided the title compound (1.95 g). MS 381 (M+18).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. washthe organic solution was washed with 5.5% HCl
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (hexanes:EtOAc 9:1 to 4:1)

출처 및 근거

ORD 기록
ord-69010a64655a4d408032c62f1cd36cf6
출처 데이터셋
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06649657B2

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