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Water → HCID 9923369、化合物

HRID 428718
ノート
印刷プレビュー

反応式

HRID 428718 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])/[C:6]/2=[CH:13]\[C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1)#[CH:2].I[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.O>CN(C)C=O.C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])/[C:6]/3=[CH:13]\[C:14]2[NH:15][CH:16]=[CH:17][CH:18]=2)=[CH:21][CH:22]=1
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 3

HCID 962WaterHCID 108944-IodophenolHCID 9813420HCID 9813420、化合物

生成物 1

HCID 9923369HCID 9923369、化合物

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物
触媒
HCID 6228Dimethylformamide溶媒
HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

A solution of (Z)-1,3-dihydro-5-ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (100 mg, 0.43 mmol) (from Example 82) and 4-iodophenol (104 mg, 0.47 mmol) (Aldrich) in N,N-dimethylformamide (2 mL) and triethylamine (2 mL) was degassed by bubbling argon through the solution for 15 minutes. Copper(I) iodide (8 mg, 0.042 mmol) (Aldrich) and (Ph3P)2PdCl2 (25 mg, 0.021 mmol) (Aldrich) were added, and the reaction was heated at 70° C. for 16 hours. Water (15 mL) was then added and the precipitate was filtered off and dried. The product was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane to give (Z)-1,3-dihydro-5-(4-hydroxyphenyl)ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a yellow powder. (Yield 121 mg, 86%).

後処理

  1. customby bubbling argon through the solution for 15 minutes
  2. filtrationthe precipitate was filtered off
  3. customdried
  4. customThe product was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-41afd9451b19465db102f418896de19a
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06313310B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート