N-Iodosuccinimide → 2-(2,4-difluorophenyl)-3-iodo-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 1930029Notes

Reaction equation

HRID 1930029 reaction equation
C1C(=O)N([I:8])C(=O)C1.[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C:17]1[N:18]=[C:19]2[CH2:24][CH2:23][CH2:22][N:20]2[CH:21]=1>CN(C=O)C>[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C:17]1[N:18]=[C:19]2[CH2:24][CH2:23][CH2:22][N:20]2[C:21]=1[I:8]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 579298552-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Product 1

HCID 579298822-(2,4-difluorophenyl)-3-iodo-6,7-dihydro-5H-pyrrolo[1,2-a]imidazoleYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NIS (6.75 g, 30.0 mmol) was added to a solution of 2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (6.61 g, 30.0 mmol) in DMF (50 mL). The reaction mixture was stirred at ambient temperature for about 35 min and then partitioned between DCM and water. The organics were dried over MgSO4, filtered, concentrated under reduced pressure, and triturated with Et2O to give the title compound (4.49 g, 43%): LC/MS (Table 1, Method a) Rt=3.18 min; MS m/z: 347.2 (M+H)+.

Workup

  1. custompartitioned between DCM and water
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customtriturated with Et2O

Sources & evidence

ORD record
ord-590de5093728471db82ab5570749c8cd
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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