N-Iodosuccinimide → 8-Chloro-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridine

HRID 456695Notes

Reaction equation

HRID 456695 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[I:18]N1C(=O)CCC1=O>ClCCl>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([I:18])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 179762858-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 695493398-Chloro-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8-Chloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridine (2 g, 8.1 mmol) was dissolved in dichloromethane (30 mL). To this solution was added N-iodosuccinimide (2.7 g, 12.1 mmol) and the resulting mixture stirred at room temperature overnight. Additional dichloromethane was added to the reaction mixture and this solution was extracted with 1 M sodium hydroxide (2×60 mL) and water, dried (magnesium sulfate), filtered and concentrated to a solid. Recrystallization from acetonitrile gave 8-chloro-2-(4-fluorophenyl)-3-iodoimidazo[1,2-α]pyridine (2.4 g, 80%) as a white solid. 1H NMR (CDCl3): δ 8.22 (d, 1H), 8.11 (q, 2H), 7.41 (d, 1H), 7.20 (t, 2H), 6.94 (t, 1H); 19F NMR (CDCl3) δ −113.2; MS m/z 373 (M+1).

Workup

  1. extractionthis solution was extracted with 1 M sodium hydroxide (2×60 mL) and water
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated to a solid
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-8f55345ac8b44dfa8aaba919e193a0f7
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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