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

HRID 330842
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인쇄 미리보기

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HRID 330842 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium
촉매
HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1dc9197ce3d74b39bd9f65ad4711d3f5
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877754B2

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