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Methyl iodide → 4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromobenzyl acetate

HRID 2172532
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HRID 2172532 반응식
CC([O-])(C)C.[K+].[C:7]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=S)[NH:19][CH2:20][Si](C)(C)C)=[CH:14][C:13]=1[Br:26])(=[O:9])[CH3:8].IC.[F:29][C:30]([F:48])([F:47])[C:31]1[CH:36]=[C:35]([C:37]([C:39]([F:42])([F:41])[F:40])=[CH2:38])[CH:34]=[C:33]([C:43]([F:46])([F:45])[F:44])[N:32]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OC)(C)(C)C>[C:7]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:38][C:37]([C:35]3[CH:36]=[C:31]([C:30]([F:29])([F:47])[F:48])[N:32]=[C:33]([C:43]([F:46])([F:44])[F:45])[CH:34]=3)([C:39]([F:42])([F:41])[F:40])[CH2:20][N:19]=2)=[CH:14][C:13]=1[Br:26])(=[O:9])[CH3:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 6328Methyl iodideHCID 2724141Tetrabutylammonium FluorideHCID 23665647Potassium tert-butoxideHCID 580920912-Bromo-4-{[(trimethylsilyl)methyl]carbamothioyl}benzyl acetateHCID 866646212,6-Bis(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine

생성물 1

HCID 86664622
4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromobenzyl acetate
수율 37.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 15413tert-Butyl methyl ether용매

실험 절차

Under argon atmosphere, t-BuOK (0.36 g) was slowly added to 2-bromo-4-{[(trimethylsilyl)methyl]carbamothioyl}benzyl acetate (1.0 g) and iodomethane (0.45 g) in THF at −10° C., and the resultant mixture was stirred for 30 minutes at the same temperature. 2,6-bis(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine (1.1 g) was added to the reaction mixture, and then n-Bu4NF in THF (0.25 ml, 1M solution) was slowly added to the mixture at −10° C. under argon atmosphere. After stirring the resultant blend for 30 minutes at the same temperature, the blend was allowed to slowly warm to room temperature. The blend was stirred at room temperature overnight. The blend was diluted with t-BuOMe, and washed with 1N HCl and brine. The organic layer was dried over MgSO4. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography to get the targeted product (0.58 g).

후처리

  1. stirringThe blend was stirred at room temperature overnight
  2. washwashed with 1N HCl and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-06f6a04c5b814e788dbacaad4f9dde3c
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09055749B2

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