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

HRID 521683
ノート
印刷プレビュー

反応式

HRID 521683 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5460b4dd5ede4b9ea643e13bc7c9d40a
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09328121B1

反応ノート

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