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Trifluoroacetic acid → {5-Fluoro-3-[3-(4-fluorobenzenesulfonyl)thiophen-2-ylmethyl]-2-methylindol-1-yl}acetic acid methyl ester

HRID 1944378
ノート
印刷プレビュー

反応式

HRID 1944378 の反応式
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[CH:21]=[C:20]1[CH3:29].[F:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([C:41]2[CH:45]=[CH:44][S:43][C:42]=2[CH:46]=O)(=[O:40])=[O:39])=[CH:34][CH:33]=1>ClCCl.ClCCCl>[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[C:21]([CH2:46][C:42]2[S:43][CH:44]=[CH:45][C:41]=2[S:38]([C:35]2[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=2)(=[O:39])=[O:40])=[C:20]1[CH3:29]
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

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 866521803-(4-Fluorobenzenesulfonyl)thiophene-2-carbaldehyde

生成物 1

HCID 67025809{5-Fluoro-3-[3-(4-fluorobenzenesulfonyl)thiophen-2-ylmethyl]-2-methylindol-1-yl}acetic acid methyl ester収率 79.1%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

A mixture of triethylsilane (0.79 g), trifluoroacetic acid (0.47 g) and 1,2-dichloroethane (2.0 mL) at −10° C. was treated dropwise with a mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (0.1 g), 3-(4-fluorobenzenesulfonyl)thiophene-2-carbaldehyde (0.15 g) and 1,2-dichloroethane (3.0 mL), and the resulting mixture was stirred at −10° C. for 15 minutes and then at room temperature overnight. The mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and dichloromethane (1:1 to 0:1 by volume) to afford the title compound as a colourless gum (0.17 g).

後処理

  1. customat room temperature
  2. customovernight
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with a mixture of cyclohexane and dichloromethane (1:1 to 0:1 by volume)

出典と根拠

ORDレコード
ord-42f6ca9cd7594bfb9478d1c37ecb500c
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08394836B2

反応ノート

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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