N-Iodosuccinimide → HCID 57929883, compound

HRID 1929974Notes

Reaction equation

HRID 1929974 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[CH:17]=1.C1C(=O)N([I:25])C(=O)C1>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:17]=1[I:25]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 22625628HCID 22625628, compound

Product 1

HCID 57929883HCID 57929883, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2,4-difluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (3.25 g, 13.9 mmol, prepared using General Procedure R from Example #8, Step A with 2-iminopiperidine hydrochloride), NIS (3.12 g, 13.9 mmol), and DMF (35 mL) was stirred at ambient temperature. After stirring overnight, the reaction mixture was partitioned between Et2O (400 mL) and water (200 mL). The organic phase was separated and dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using heptane/EtOAc (gradient from 100:0 to 0:100) to give the title compound (3.44 g, 69%). LC/MS (Table 1, Method a) Rt=3.32 min; MS m/z: 361.0 (M+H)+.

Workup

  1. customthe reaction mixture was partitioned between Et2O (400 mL) and water (200 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c78fae9e806d480bb423d19725e77b03
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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