Ethyl 3-phenylprop-2-enoate → 3-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

HRID 1716656ノート

反応式

HRID 1716656 の反応式
Br[C:2]1[C:10]([O:11][CH3:12])=[CH:9][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>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:24]([O:23][C:13](=[O:22])[CH:14]=[C:15]([C:2]1[C:10]([O:11][CH3:12])=[CH:9][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 220305584-bromo-5-methoxy-1H-indole

生成物 1

HCID 673557843-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 4-bromo-5-methoxyindole XLVI (104 mg, 0.46 mmol), ethyl cinnamate (162 mg, 0.92 mmol), tetra-butylammonium bromide (29.6 mg, 0.092 mmol), TEA (128 μl, 0.092 mmol) and palladium-dichloro-[bis(tri-ortho-tolyl)phosphine] (18 mg, 0.023 mmol) in DMF (2 ml) was stirred at 110° C. for 3 hours. The reaction mixture was cooled to room temperature and partitioned between brine and EtOAc. The organic layers were combined, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 3-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester XLVIII (37 mg, impure).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between brine and EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via flash chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-de25483c87aa465fa2fffdb9c5947f44
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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