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

HRID 71833Notes

Reaction equation

HRID 71833 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d7ce7cf331b84e96a50a523c59f59f68
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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