N-Iodosuccinimide → 2-Chloro-6-fluoro-3-iodoimidazo[1,2-A]pyridine

HRID 705072Notes

Reaction equation

HRID 705072 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[CH:11]=1.[I:12]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1[I:12]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 552678642-Chloro-6-fluoroimidazo[1,2-A]pyridine

Product 1

HCID 717433442-Chloro-6-fluoro-3-iodoimidazo[1,2-A]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the title compound from Example 2 Step B (1.0 g, 5.86 mmol) in acetonitrile (29.3 mL) was added N-iodosuccinimide (1.583 g, 7.04 mmol). The resulting mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (10-30% ethyl acetate in hexanes) provided the title compound: LCMS m/z 296.70 [M+H]+, 298.65 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.03 (t, J=2.8 Hz, 1H), 7.56-7.51 (m, 1H), 7.22-7.18 (m, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel (10-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0875119397c24a428376bd3bfae1ea14
Source dataset
uspto-grants-2015_11
Patent number
US09173873B2

Reaction notes

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