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

HRID 2039077Notes

Reaction equation

HRID 2039077 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) Solid
  4. filtrationwas collected by vacuum filtration
  5. washwashed with dichloromethane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-22404f7bc3b54453a8f6694d1af73941
Source dataset
uspto-grants-2013_11
Patent number
US08575118B2

Reaction notes

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