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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Trifluoroacetic acid → 2-[{5-Fluoro-7-[(methylsulfonyl)methyl]-1H-indol-3-yl}(4-methylphenyl)methyl]cyclopropane-carbonitrile

HRID 561682
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HRID 561682 반응식
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=1)[NH:18][CH:17]=[CH:16]2.O[CH:28]([C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1)[CH:29]1[CH2:31][CH:30]1[C:32]#[N:33]>ClCCCl.ClCCl>[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([CH2:22][S:23]([CH3:26])(=[O:24])=[O:25])[CH:21]=1)[NH:18][CH:17]=[C:16]2[CH:28]([C:34]1[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=1)[CH:29]1[CH2:31][CH:30]1[C:32]#[N:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583923185-Fluoro-7-[(methylsulfonyl)methyl]-1H-indoleHCID 583923442-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

생성물 1

HCID 583925252-[{5-Fluoro-7-[(methylsulfonyl)methyl]-1H-indol-3-yl}(4-methylphenyl)methyl]cyclopropane-carbonitrile

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매
HCID 6344Dichloromethane용매

실험 절차

3.63 g (16.4 mmol) of indium(III) chloride and 1.9 ml (24.6 mmol) of trifluoroacetic acid were added to 4.23 g (16.4 mmol) of the compound from Example 87A and 2.56 g (13.7 mmol) of the compound from Example 158A under argon in 300 ml of 1,2-dichloroethane, and the mixture was stirred under reflux for 4 h. It was diluted with dichloromethane and washed with water and saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 3.16 g (49% of theory) of the title compound as mixture of diastereomers.

후처리

  1. temperatureunder reflux for 4 h
  2. washwashed with water and saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

출처 및 근거

ORD 기록
ord-18e1deab0be44731af3ce5d2d63a79a6
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063234B2

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