Trifluoroacetic acid → 5-(4-bromo-naphthalen-1-yl)-2-pyrrolidin-2-yl-1H-imidazole

HRID 1185744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185744
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:14][C:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([Br:28])=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:28][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([C:15]2[NH:14][C:13]([CH:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[N:17][CH:16]=2)=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 666204542-[5-(4-Bromo-naphthalen-1-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 666201165-(4-bromo-naphthalen-1-yl)-2-pyrrolidin-2-yl-1H-imidazoleAusbeute 121,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-[5-(4-Bromo-naphthalen-1-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g) was dissolved in DCM (12 mL), and trifluoroacetic acid (4 mL) was added. The reaction mixture was stirred at ambient temperature for 3 hours and evaporated under vacuum. Solid was dissolved in DCM (10 mL) and extracted with saturated NaHCO3 solution (30 mL). A solid was collected by vacuum filtration, washed with DCM, and dried under vacuum, giving 5-(4-bromo-naphthalen-1-yl)-2-pyrrolidin-2-yl-1H-imidazole (0.940 g, crude) as an off-white solid.

Aufarbeitung

  1. customevaporated under vacuum
  2. dissolutionSolid was dissolved in DCM (10 mL)
  3. extractionextracted with saturated NaHCO3 solution (30 mL)
  4. filtrationA solid was collected by vacuum filtration
  5. washwashed with DCM
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9c769135d58c4e6f862a08a26b6ae42b
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669234B2

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