Trifluoroacetic acid → 5-(6-Bromo-naphthalen-2-yl)-2-pyrrolidin-2-yl-1H-imidazole

HRID 71833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 71833
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Br:28])[CH:24]=3)[CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br:28][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:15]1[NH:14][C:13]([CH:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[N:17][CH:16]=1)[CH:27]=[CH:26]2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 58185449tert-butyl (2S)-2-[5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

Produkt 1

HCID 666207675-(6-Bromo-naphthalen-2-yl)-2-pyrrolidin-2-yl-1H-imidazoleAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-[5-(6-Bromonaphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (5.03 g) was dissolved in dichloromethane (75 mL), and trifluoroacetic acid (25 mL) was added. The reaction mixture was stirred at ambient temperature for 5 hours and evaporated under vacuum. Solid was dissolved in dichloromethane (50 mL) and extracted with saturated NaHCO3 solution (50 mL). Solid was collected by vacuum filtration, washed with dichloromethane, and dried under vacuum, giving 5-(6-Bromo-naphthalen-2-yl)-2-pyrrolidin-2-yl-1H-imidazole (98%) as an off-white solid.

Aufarbeitung

  1. customevaporated under vacuum
  2. dissolutionSolid was dissolved in dichloromethane (50 mL)
  3. extractionextracted with saturated NaHCO3 solution (50 mL)
  4. filtrationSolid was collected by vacuum filtration
  5. washwashed with dichloromethane
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d7ce7cf331b84e96a50a523c59f59f68
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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