Water → 7-Ethenyl-1H-indole

HRID 1725365노트

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HRID 1725365 반응식
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.[Cl-].[Li+].Br[C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[NH:26][CH:25]=[CH:24]2.O>CN(C)C=O.C1([Pd-2](Cl)(Cl)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[CH:1]([C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[NH:26][CH:25]=[CH:24]2)=[CH2:2]

참가 물질

9

반응물 4

HCID 962WaterHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 27570207-Bromoindole

생성물 1

HCID 145674047-Ethenyl-1H-indole수율 80%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 178479785HCID 178479785, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

Add tributyl(vinyl)tin (9.8 mL, 33.7 mmol), triphenyl-phosphine (0.4 g, 1.53 mmol), diphenylpalladium(II) dichloride (1.07 g, 1.53 mmol) and lithium chloride (4.0 g, 94.4 mmol) to 7-bromo-1H-indole (6.0 g, 30.6 mmol) in 150 mL of dimethylformamide and heat the resulting mixture at 100° C. overnight. Cool the reaction mixture to 20-24° C. and poured into a mixture of 150 mL of water and 150 mL of ethyl acetate. Wash the aqueous layer with additional ethyl acetate (3×100 mL), combine the organic layers, wash with saturated aqueous sodium chloride, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 5-10% ethyl acetate in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the desired compound as a clear oil (3.5 g, 80%).

후처리

  1. temperatureCool the reaction mixture to 20-24° C.
  2. washWash the aqueous layer with additional ethyl acetate (3×100 mL)
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. washeluting with 5-10% ethyl acetate in hexanes
  8. additionCombine fractions containing product
  9. concentrationconcentrate them under reduced pressure

출처 및 근거

ORD 기록
ord-3d9f319d78ae4275ac7914eb7d7fbe87
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491716B2

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