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Sodium hydride → 3-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one

HRID 2120228
ノート
印刷プレビュー

反応式

HRID 2120228 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[NH:14][C:15]([CH3:19])=[CH:16][C:17]=2[CH3:18])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29].N1CCCC1.[H-].[Na+]>N12CCCN=C1CCCCC2.CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[NH:14][C:15]([CH3:19])=[CH:16][C:17]=2[CH3:18])=[C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:20][C:21]2=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
参加物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 24758Sodium hydrideHCID 31268PyrrolidineHCID 321710OxindoleHCID 23439089(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone

生成物 1

HCID 539061583-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one収率 3.3%

試薬・触媒・溶媒 3

HCID 81184
1,8-Diazabicyclo(5.4.0)undec-7-ene
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

(3,4-Dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone (100 mg, 0.4 mmol), oxindole (100 mg, 0.8 mmol), pyrrolidine (0.2 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (a few drops) in dimethylforamide (1.5 mL) was heated at 160° C. for 2 hours. Sodium hydride (18 mg) was added to the reaction mixture and the heating was continued at 160° C. for 3 days. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was chromatographed eluting with ethyl acetate and hexane to give 5 mg of 3-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one. MS EI 374 [M]+.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed
  6. washeluting with ethyl acetate and hexane

出典と根拠

ORDレコード
ord-7260a3583a434f72b910d5777a6ab168
出典データセット
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06689806B1

反応ノート

読み込み中…

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