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Water → 1-(4-difluoromethoxybenzenesulfonyl)-5-iodo-1H-indole

HRID 1890364
ノート
印刷プレビュー

反応式

HRID 1890364 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[F:13][CH:14]([F:26])[O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>CN(C)C=O>[F:26][CH:14]([F:13])[O:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([I:1])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:24])=[O:23])=[CH:20][CH:21]=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

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27782234-(Difluoromethoxy)benzenesulfonyl chlorideHCID 27823135-Iodo-1H-indole

生成物 1

HCID 685969371-(4-difluoromethoxybenzenesulfonyl)-5-iodo-1H-indole収率 81.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒
2 回

反応条件

温度
0 °C

実験手順

5-Iodo-1H-indole (2.0 g, 8.23 mmol) was dissolved in dimethylformamide (DMF) (10 ml) and cooled to 0° C. Sodium hydride (494 mg, 12.34 mmol) was added in small portions. The reaction mixture was stirred for 1 hour at 0° C. 4-(Difluoro-methoxy)-benzenesulfonyl chloride (2.196 g, 9.05 mmol) was dissolved in DMF (5 ml), and added slowly to the reaction mixture. Stirring was continued for 45 minutes. Cold water (150 ml) was added to the reaction mixture. The reaction mixture was extracted twice with ethyl acetate (100 ml). The organic layer was dried over magnesium sulphate, filtered, and the solvent evaporated under reduced pressure to give a crystalline solid (3.0 g, 81%). ESI-MS [m/z]: 449.95 [M+H]+. 1H-NMR (500 MHz, d6-DMSO): δ=8.05 (d, 2H), 8.0 (s, 1H), 7.85 (d, 1H), 7.8 (d, 1H), 7.65 (d, 1H), 7.4 (t, J=70 Hz, 1H), 7.35 (d, 2H), 6.8 ppm (d, 1H).

後処理

  1. additionadded slowly to the reaction mixture
  2. stirringStirring
  3. waitwas continued for 45 minutes
  4. extractionThe reaction mixture was extracted twice with ethyl acetate (100 ml)
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

出典と根拠

ORDレコード
ord-f769e013773543daa41273c834202e0a
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507469B2

反応ノート

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