Trifluoroacetic acid → 5-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate

HRID 46167Notes

Reaction equation

HRID 46167 reaction equation
C([O:5][C:6](=[O:27])[CH2:7][C:8]1([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2=[N:17][CH:18]=[CH:19][N:9]12)(C)(C)C.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>C(Cl)Cl>[F:28][C:29]([F:34])([F:33])[C:30]([O-:32])=[O:31].[Br:26][C:23]1[CH:24]=[CH:25][C:20]([C:8]2([CH2:7][C:6]([OH:27])=[O:5])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3=[NH+:17][CH:18]=[CH:19][N:9]23)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58415621HCID 58415621, compound

Product 1

HCID 1785249895-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]acetate (3.22 g) in CH2Cl2 (10 mL) was added trifluoroacetic acid (10 mL). The reaction mixture was concentrated after stirring at room temperature for 6 h. The viscous material was dissolved in MeCN-water and lyophilized to a sticky solid. This material when dissolved and concentrated from toluene (3×) afforded the title compound as a white solid. Mass. found (M+H)+, 371.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe viscous material was dissolved in MeCN-water
  3. dissolutionThis material when dissolved
  4. concentrationconcentrated from toluene (3×)

Sources & evidence

ORD record
ord-99c1afac3340485ba1f251ac49a540f2
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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