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Trifluoroacetic acid → 2-[1-(4-Chlorophenyl)-1-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}ethyl]cyclopropanecarbonitrile

HRID 561629
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HRID 561629 반응식
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:22]2[CH2:24][CH:23]2[C:25]#[N:26])(O)[CH3:20])=[CH:15][CH:14]=1.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[C:35]([CH2:37][S:38][CH3:39])[CH:36]=1)[NH:33][CH:32]=[CH:31]2>ClCCl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:22]2[CH2:24][CH:23]2[C:25]#[N:26])([C:31]2[C:30]3[C:34](=[C:35]([CH2:37][S:38][CH3:39])[CH:36]=[C:28]([F:27])[CH:29]=3)[NH:33][CH:32]=2)[CH3:20])=[CH:15][CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583923532-[1-(4-Chlorophenyl)-1-hydroxyethyl]cyclopropanecarbonitrile

생성물 1

HCID 583923982-[1-(4-Chlorophenyl)-1-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}ethyl]cyclopropanecarbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

367 mg (1.66 mmol) of indium(III) chloride and 0.12 ml (1.58 mmol) of trifluoroacetic acid were added to 350 mg (1.58 mmol) of the compound from Example 75A and 308 mg (1.58 mmol) of the compound from Example 11A in 9 ml of dichloromethane at RT, and the mixture was heated under reflux for 15 min. It was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride 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 32.5 mg (5% of theory) of the title compound as mixture of diastereomers.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 min
  3. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. 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-891e9740aaff47efafd63ad8357f1b45
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063234B2

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