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

HRID 1716656노트

반응식

HRID 1716656 반응식
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]

참가 물질

5

반응물 2

HCID 7649Ethyl 3-phenylprop-2-enoateHCID 220305584-bromo-5-methoxy-1H-indole

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-de25483c87aa465fa2fffdb9c5947f44
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803830B2

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