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Cesium carbonate → 5-(3-Cyano-4-phenylpyrrole-1-yl)-2-methoxymethoxy-benzoic acid ethyl ester

HRID 1516594
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HRID 1516594 반응식
[C:1]1([C:7]2[C:8]([C:12]#[N:13])=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22](Br)[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][O:27][CH3:28])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu](I)I.CS(C)=O>[CH2:14]([O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22]([N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]([C:12]#[N:13])=[CH:9]2)[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][O:27][CH3:28])[CH3:15]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 37214604-Phenyl-1H-pyrrole-3-carbonitrileHCID 594778785-Bromo-2-methoxymethoxy-benzoic acid ethyl ester

생성물 1

HCID 594776895-(3-Cyano-4-phenylpyrrole-1-yl)-2-methoxymethoxy-benzoic acid ethyl ester수율 60.3%

시약·촉매·용매 2

HCID 83717Copper iodide촉매
HCID 679
Dimethyl Sulfoxide
용매

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온도
75 °C

실험 절차

A mixture of 4-phenyl-1H-pyrrole-3-carbonitrile (0.2 g), 5-bromo-2-methoxymethoxy-benzoic acid ethyl ester (0.36 g), copper iodide (0.023 g), N,N-dimethylgrycine (0.025 g), cesium carbonate (0.39 g) and dimethylsulfoxide (3 mL) was stirred at 75° C. for 12 hours. After cooling to ambient temperature, the insoluble material was removed by filtration through Celite pad, and this filtrate was concentrated. This obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90−66/34) to give the title compound (0.27 g).

후처리

  1. temperatureAfter cooling to ambient temperature
  2. customthe insoluble material was removed by filtration through Celite pad
  3. concentrationthis filtrate was concentrated
  4. customThis obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90−66/34)

출처 및 근거

ORD 기록
ord-cf9eb2336b524ebd9a0701921e5c7ca6
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08227500B2

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