Sodium Iodide → HCID 86615144, compound

HRID 1009392Notes

Reaction equation

HRID 1009392 reaction equation
[I-].[Na+].[N-:3]=[N+:4]=[N-:5].[Na+].Cl[CH2:8][CH2:9][CH2:10]/[C:11](/[C:27]1[O:28][C:29]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[N:30][N:31]=1)=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]2)=[C:15]([O:25][CH3:26])[CH:14]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:3]([CH2:8][CH2:9][CH2:10]/[C:11](/[C:27]1[O:28][C:29]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)=[N:30][N:31]=1)=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]2)=[C:15]([O:25][CH3:26])[CH:14]=1)=[N+:4]=[N-:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 67067431HCID 67067431, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 86615144HCID 86615144, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Sodium iodide (35 mg) and sodium azide (20 mg) were added to a solution of 2-{4-chloro-1-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}butyl}-5-(4-fluorobenzyl)[1,3,4]oxadiazole (72 mg) in DMF (2 mL), and the reaction solution was stirred at 80° C. for five hours. The reaction solution was left to cool to room temperature. Then, ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=3:1->ethyl acetate) to obtain 50 mg of the title compound. The property values of the compound are as follows.

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=3:1->ethyl acetate)

Sources & evidence

ORD record
ord-a469553912ca47f88051ffcff965c339
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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