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

HRID 79784Notes

Reaction equation

HRID 79784 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-7b936ec034eb467dbbbb437bfe168dc7
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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