Methanol → HCID 58243590, compound

HRID 389155Notes

Reaction equation

HRID 389155 reaction equation
CO.C[C:4](C)([O-:6])C.[K+].F[C:10]1[CH:17]=[C:16]([C:18]2[N:22]([CH3:23])[C:21]([C:24]([CH3:36])([O:26][C:27]3[C:32]([F:33])=[CH:31][C:30]([F:34])=[CH:29][C:28]=3[F:35])[CH3:25])=[N:20][N:19]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13].O>C1COCC1>[CH3:4][O:6][C:10]1[CH:17]=[C:16]([C:18]2[N:22]([CH3:23])[C:21]([C:24]([CH3:36])([O:26][C:27]3[C:32]([F:33])=[CH:31][C:30]([F:34])=[CH:29][C:28]=3[F:35])[CH3:25])=[N:20][N:19]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 58243902HCID 58243902, compound

Product 1

HCID 58243590HCID 58243590, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanol (0.060 ml) was added to a solution of potassium tert-butoxide (130 mg) in THF (6 ml) under ice cooling, followed by stirring for 15 minutes under ice cooling. 2-fluoro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}benzonitrile (300 mg) was added to the reaction mixture, followed by stirring for one hour, while slowly elevating to room temperature. Water was added to the reaction solution, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was then evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 30:70 linear gradient) to obtain 2-methoxy-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}benzonitrile (192 mg), as a colorless solid.

Workup

  1. stirringby stirring for one hour
  2. customwhile slowly elevating to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was then evaporated
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 30:70 linear gradient)

Sources & evidence

ORD record
ord-aee5de1945294afd969c9fd4817403dd
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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