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

HRID 2039068Notes

Reaction equation

HRID 2039068 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[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

Participants

4

Reactant 2

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

Product 1

HCID 666201165-(4-bromo-naphthalen-1-yl)-2-pyrrolidin-2-yl-1H-imidazoleYield 121.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5c653f6f47e64eba816f020907a60b90
Source dataset
uspto-grants-2013_11
Patent number
US08575118B2

Reaction notes

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