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1,4-Dioxane → 6-(2-Ethylsulfanylphenyl)-2-trifluoromethylimidazo[1,2-a]pyridine

HRID 521683
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HRID 521683 반응식
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B1OC(C)(C)C(C)(C)O1)[CH3:2].Br[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=2)[CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(OCC)(=O)C>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([CH:26]=[C:27]([C:29]([F:31])([F:32])[F:30])[N:28]=2)[CH:25]=1)[CH3:2]
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참가 물질

8

반응물 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 199734446-Bromo-2-(trifluoromethyl)imidazo(1,2-a)pyridineHCID 1237879692-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 725490316-(2-Ethylsulfanylphenyl)-2-trifluoromethylimidazo[1,2-a]pyridine수율 44.3%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

A mixture of 0.53 g of 2-ethylsulfanylphenylboronic acid pinacol ester, 0.52 g of 6-bromo-2-trifluoromethylimidazo[1,2-a]pyridine, 0.02 g of tris(dibenzylideneacetone)dipalladium(0), 0.05 g of 2-dicyclohexylphosphino-2′,6′-dimethoxyphenyl, 0.84 g of tripotassium phosphate and 6 ml of 1,4-dioxane was stirred at 110° C. for 7 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The filtrate was extracted with ethyl acetate and then dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.28 g of 6-(2-ethylsulfanylphenyl)-2-trifluoromethylimidazo[1,2-a]pyridine (Compound of Present Invention 26).

후처리

  1. filtrationthe mixture was filtered
  2. extractionThe filtrate was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5460b4dd5ede4b9ea643e13bc7c9d40a
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09328121B1

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