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Toluene → 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine

HRID 1750059
ノート
印刷プレビュー

反応式

HRID 1750059 の反応式
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:10]=[C:5]2[N:4]=[CH:3]1.Br[C:19]1[CH:24]=[CH:23][C:22]([S:25][C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=1[S:30][CH2:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>[CH2:31]([S:30][C:20]1[CH:21]=[C:22]([S:25][C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:24][C:19]=1[C:3]1[N:2]([CH3:1])[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:10]=[C:5]2[N:4]=1)[CH3:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 1180352773-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridineHCID 1180355631-Bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene

生成物 1

HCID 1180356092-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine収率 82.4%

試薬・触媒・溶媒

5
HCID 11776Triphenylphosphine触媒HCID 165397Cupric acetate monohydrate触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 0.12 g of 3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine, 0.15 g of 1-bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene, 0.01 g of palladium(II) acetate, 0.01 g of triphenylphosphine, 0.02 g of copper(II) acetate monohydrate, 0.13 g of potassium carbonate and 3 ml of toluene was stirred under heating and refluxing for 2 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 0.19 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound 8).

後処理

  1. temperatureunder heating
  2. temperaturerefluxing for 2 hours
  3. filtrationthe mixture was filtered
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe mixture was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-21d1dffe809c4bd296363b006f79ba2f
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156838B2

反応ノート

読み込み中…

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