Ethyl 3-phenylprop-2-enoate → 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

HRID 1716692ノート

反応式

HRID 1716692 の反応式
Br[C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:13]([O:23][CH2:24][CH3:25])(=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:24]([O:23][C:13](=[O:22])[CH:14]=[C:15]([C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:25]

参加物

5

反応物 2

HCID 7649Ethyl 3-phenylprop-2-enoateHCID 247280264-bromo-6-methoxy-1H-indole

生成物 1

HCID 673560903-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-bromo-6-methoxy-indole CXIV (920 mg, 4.1 mmol), ethyl cinnamate (1.03 ml, 6.1 mmol), TEA (850 μl, 6.1 mmol), Pd(OAc)2 (46 mg, 0.20 mmol) and (o-Tol)3P (120 mg, 0.41 mmol) was heated in a sealed vial to 100° C. for 27 hours; The reaction mixture was cooled to room temperature, diluted with DCM, and the mixture was filtered through celite. The filtrate was concentrated and purified via flash chromatography (hexane/EtOAc) to afford 3-(6-methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester CXVI as a yellow-brown waxy solid (440 mg, 34% yield).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated
  4. custompurified via flash chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-8ec1051f90f84aa9b37030d9ef963e02
出典データセット
uspto-grants-2010_09
特許番号
US07803830B2

反応ノート

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