N-Iodosuccinimide → 6-Chloro-1-iodo-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

HRID 2203342Notes

Reaction equation

HRID 2203342 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[N:9][CH:10]=2)[CH:7]=1.C1C(=O)N([I:27])C(=O)C1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[N:9][C:10]=2[I:27])[CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 866789776-Chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

Product 1

HCID 866789786-Chloro-1-iodo-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate from Step G (3.64 g, 12.19 mmol) in anhydrous DCM (50 mL) was added NIS (5.48 g, 24.4 mmol). The reaction mixture was stirred at room temperature for 18 hours and concentrated. The residue was suspended in ethyl acetate and washed with saturated sodium thiosulfate (2×). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give a bright white solid. m/z=424.7 (M+H).

Workup

  1. concentrationconcentrated
  2. washwashed with saturated sodium thiosulfate (2×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. customto give a bright white solid

Sources & evidence

ORD record
ord-5094bc3808084fb6a8c49fd0f2f919aa
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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