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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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 Tert-butyl Ester

HRID 890821
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HRID 890821 반응식
[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[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>[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:17]=[CH:16][N:18]1[C:19](=[O:28])[C:20]2[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:23])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

8

반응물 4

HCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 53936336Tert-butyl 2-(3-bromophenyl)acetate

생성물 1

HCID 53900851{2-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-vinyl]-phenyl}-acetic Acid Tert-butyl Ester수율 25.8%

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 tri-o-tolylphosphine (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-a5cc08aa49c54c228d56be16cb867e2a
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06998423B2

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