Ethyl Acetate → HCID 10271121, compound

HRID 584744Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C: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]([C:13]2[N: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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(4-methoxyphenyl)-5-(6-methoxypridin-3-yl)-1H-1,2,4-triazol-3-ol (200 mg, 0.67 mmol), potassium carbonate (278 mg, 2.01 mmol), and 2-iodo-1,1,1-trifluoroethane (0.198 mL, 2.01 mmol) in dimethylsulfoxide (1 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 10:1). The desired product was washed with hexane to give 2-methoxy-5-(1-(4-methoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazole-5-yl)pyridine. (60 mg, 23.5% yield)

Workup

temperatureAfter cooling
customthe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was purified by column chromatography (toluene-ethyl acetate 10:1)
washThe desired product was washed with hexane

Sources & evidence

ORD record: ord-98adea1a5a79478ea92a757eb3d5b0e6
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06927230B2

Reaction notes

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