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Trifluoroacetic acid → [5-Fluoro-2-methyl-3-(2-sulfobenzyl)indol-1-yl]acetic acid methyl ester

HRID 1944425
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HRID 1944425 반응식
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:15].[Na+].[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([O-:29])(=[O:28])=[O:27])=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:18][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[S:26]([OH:29])(=[O:28])=[O:27])=[C:6]1[CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 3794540Sodium o-formylbenzenesulfonateHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetate

생성물 1

HCID 86652190[5-Fluoro-2-methyl-3-(2-sulfobenzyl)indol-1-yl]acetic acid methyl ester수율 73.6%

시약·촉매·용매 1

HCID 11
1,2-Dichloroethane
용매
2회

실험 절차

A mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (1.0 g), 2-formylbenzensulfonic acid sodium salt (0.94 g) and 1,2-dichloroethane (15 mL) at 0° C. was treated dropwise with a mixture of triethylsilane (4.3 mL), trifluoroacetic acid (1.0 mL) and 1,2-dichloroethane (10 mL), and the resulting mixture was stirred at room temperature for 6 hours. The mixture was extracted with ethyl acetate and the combined organic extract was dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (0:1 to 1:9 by volume) to afford the title compound as a purple gum (1.3 g).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionthe combined organic extract
  3. dry with materialwas dried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of methanol and dichloromethane (0:1 to 1:9 by volume)

출처 및 근거

ORD 기록
ord-e70b1af3948540bb810480d9cc1aec39
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394836B2

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