Methyl iodide → 5-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole

HRID 599572Notes

Reaction equation

HRID 599572 reaction equation
O.[Na].[F:3][C:4]1[CH:31]=[CH:30][C:7]([CH2:8][C:9]2[NH:13][C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)=[N:11][N:10]=2)=[CH:6][CH:5]=1.IC.O.[C:35](=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[N:10]([CH3:35])[N:11]=[C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)[N:13]=2)=[CH:30][CH:31]=1.[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[N:13]=[C:12](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)[N:11]([CH3:35])[N:10]=2)=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 71353970Sodium monohydrateHCID 86585896Sodium bicarbonate waterHCID 178489917HCID 178489917, compound

Product 2

HCID 248526785-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazoleHCID 24852780HCID 24852780, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydrate (containing mineral oil at 60%, 6 mg) was added to a solution of 3-(4-fluorobenzyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-4H-[1,2,4]triazole (18 mg) in THF (1 mL), and the reaction solution was stirred at room temperature for 30 minutes. Iodomethane (20 mg) was added to the reaction solution, and the reaction solution was then stirred at room temperature for 1.5 hours. 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 (elution solvent: ethyl acetate:ethanol=9:1) to obtain 6 mg of 5-(4-fluorobenzyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole and 2 mg of 3-(4-fluorobenzyl)-5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1-methyl-1H-[1,2,4]triazole.

Workup

  1. stirringthe reaction solution was then stirred at room temperature for 1.5 hours
  2. customthe organic layer was separated
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate:ethanol=9:1)

Sources & evidence

ORD record
ord-e8680f22d5cd427a8cadffdd1508b595
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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