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1-Ethynyl-4-methoxybenzene → N-Ethyl-2-[4-(4-methoxy-phenylethynyl)-phenyl]-propionamide

HRID 330842
ノート
印刷プレビュー

反応式

HRID 330842 の反応式
[CH2:1]([NH:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)#[CH:16]>C(#N)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.CCOC(C)=O>[CH2:1]([NH:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:16]#[C:15][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)[CH3:6])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 66693450N-Ethyl-2-(4-iodo-phenyl)-propionamide

生成物 1

HCID 56929774N-Ethyl-2-[4-(4-methoxy-phenylethynyl)-phenyl]-propionamide

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium
触媒
HCID 6342Acetonitrile溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

300 mg (0.99 mmol) N-Ethyl-2-(4-iodo-phenyl)-propionamide (XVIII.1) are added to 148 μL (1.14 mmol) 1-ethynyl-4-methoxybenzene in 8 mL ACN under inert gas atmosphere. 276 μL (1.99 mmol) TEA as base, 6 mg (0.03 mmol) copper(I)iodide and 42 mg (0.060 mmol) bis(triphenylphosphine)palladium(II)chloride as catalyst are added and the mixture is stirred at rt under inert gas atmosphere for 5 h. After that time, the mixture is diluted with EtOAc, washed with saturated ammonium chloride solution and brine, and the organic layer is dried over sodium sulphate. The solvent is evaporated and the residue is purified by column chromatography (silicia gel; heptane:EtOAc 50:50).

後処理

  1. washwashed with saturated ammonium chloride solution and brine
  2. dry with materialthe organic layer is dried over sodium sulphate
  3. customThe solvent is evaporated
  4. customthe residue is purified by column chromatography (silicia gel; heptane:EtOAc 50:50)

出典と根拠

ORDレコード
ord-1dc9197ce3d74b39bd9f65ad4711d3f5
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877754B2

反応ノート

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