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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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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2172532
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]
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Komponenten

8

Edukt 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

Produkt 1

HCID 86664622
4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromobenzyl acetate
Ausbeute 37,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-06f6a04c5b814e788dbacaad4f9dde3c
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09055749B2

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