5-(4-bromophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol → 5-(4-Bromophenyl)-5H-imidazo[2,1-A]isoindole

HRID 46161Notes

Reaction equation

HRID 46161 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3=[N:17][CH2:18][CH2:19][N:9]23)=[CH:4][CH:3]=1>CC(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3=[N:17][CH:18]=[CH:19][N:9]23)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 104042835-(4-bromophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol

Product 1

HCID 584155145-(4-Bromophenyl)-5H-imidazo[2,1-A]isoindole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-(4-bromophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol (20.5 g) in AcOH (210 mL) was heated at 125° C. under nitrogen for 6.5 h. The reaction mixture was the cooled to room temperature and concentrated. The resulting residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution. Aqueous layer was extracted with EtOAc (2×). Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. Flash chromatography using a linear gradient of 0-4% MeOH in EtOAc-hexanes (1:1, v/v) afforded title compound as a light yellow solid. Mass. found (M+H)+, 311.0.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. extractionAqueous layer was extracted with EtOAc (2×)
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f253f5d25872494c90b4b76052da6916
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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