Water → 7-Ethenyl-1H-indole

HRID 557168

反応式

HRID 557168 の反応式
[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]

参加物

9

反応物 4

HCID 962WaterHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 27570207-Bromoindole

生成物 1

HCID 145674047-Ethenyl-1H-indole収率 80%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 178479785HCID 178479785、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-968e909d4d174403abf46155922e6b3a
出典データセット
uspto-grants-2011_11
特許番号
US08058425B2

関連ノート

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