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Toluene → 2-Methyl-4-{(E)-2-[5-(3-trifluoromethyl phenyl)pyridin-2-yl]vinyl}octahydropyrrolo[3,4-a]indolizine-1,3-dione

HRID 540642
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HRID 540642 반응식
Br[C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[CH:10]2[N:18]3[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH:12]3[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[CH:11]23)=[N:6][CH:7]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH3:23][N:20]1[C:21](=[O:22])[CH:11]2[CH:10](/[CH:9]=[CH:8]/[C:5]3[CH:4]=[CH:3][C:2]([C:31]4[CH:30]=[CH:29][CH:28]=[C:27]([C:26]([F:37])([F:36])[F:25])[CH:32]=4)=[CH:7][N:6]=3)[N:18]3[CH:13]([CH:12]2[C:19]1=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17]3
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참가 물질

8

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 534923684-[(E)-2-(5-bromopyridin-2-yl)vinyl]-2-methyloctahydropyrrolo[3,4-a]-indolizine-1,3-dione2회

생성물 1

HCID 534925042-Methyl-4-{(E)-2-[5-(3-trifluoromethyl phenyl)pyridin-2-yl]vinyl}octahydropyrrolo[3,4-a]indolizine-1,3-dione

시약·촉매·용매

3
HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회

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온도
100 °C

실험 절차

A mixture consisting of 42 mg of 4-[(E)-2-(5-bromopyridin-2-yl)vinyl]-2-methyloctahydropyrrolo[3,4-a]indolizine-1,3-dione (from Example 6, racemic mixture 1), 2.5 mg of tetrakis(triphenylphosphine)palladium(0), 25 mg of 3-trifluoromethylphenylboronic acid, 37 mg of potassium carbonate, 1.5 ml of toluene, 0.3 ml of ethanol and 0.75 ml of water is stirred at 100° C. for 5 h. After cooling, the mixture is taken up in 20 ml of water and the product is extracted by shaking with 20 ml of ethyl acetate. After drying and concentration of the organic phase, an oil is obtained. The crude product is purified by column chromatography (silica gel, MeOH:DCM=1:99).

후처리

  1. temperatureAfter cooling
  2. extractionthe product is extracted
  3. stirringby shaking with 20 ml of ethyl acetate
  4. customAfter drying
  5. customconcentration of the organic phase, an oil is obtained
  6. customThe crude product is purified by column chromatography (silica gel, MeOH:DCM=1:99)

출처 및 근거

ORD 기록
ord-c03b55e0e8994cbd9c671a03778f8265
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871798B2

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