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Ethyl Acetate → HCID 10156604, compound

HRID 584748
Notes
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Reaction equation

HRID 584748 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=[C:11]([OH:22])[N:10]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:30][C:31]([F:34])([F:33])[F:32].C(OCC)(=O)C>CS(C)=O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[N:10][C:11]([O:22][CH2:30][C:31]([F:34])([F:33])[F:32])=[N:12]2)=[CH:15][N:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 178489016HCID 178489016, compound

Product 1

HCID 10156604HCID 10156604, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-methoxyphenyl)-1-(6-methoxypyridin-3-yl)-1H-1,2,4-triazol-3-ol (300 mg, 1.01 mmol), potassium carbonate (417 mg, 3.02 mmol), and 2-iodo-1,1,1-trifluoroethane (0.496 mL, 5.03 mmol) in dimethyl sulfoxide (1.5 mL) were heated at 100° C. for 1 hour. After cooling, ice water and ethyl acetate were poured into the mixture and the organic layer was separated, washed with brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography (toluene-ethyl acetate 8:1) The desired product was washed with hexane to give 2-methoxy-5-(5-(4-methoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazol-1-yl)pyridine (175 mg, 45.8% yield).

Workup

  1. temperatureAfter cooling
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography (toluene-ethyl acetate 8:1) The desired product
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-b4cea31b056f43359aed943f4e5f596f
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06927230B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes