Water → HCID 57378558, compound

HRID 1258878Notes

Reaction equation

HRID 1258878 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([CH3:18])[C:12]=2[C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)=[CH:4][CH:3]=1.[CH3:19][C:20]([C:22]1[CH:27]=[CH:26][C:25](F)=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([CH3:18])[C:12]=2[C:13]2[N:14]=[CH:15][N:16]([C:25]3[CH:26]=[CH:27][C:22]([C:20](=[O:21])[CH3:19])=[CH:23][CH:24]=3)[CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 178481995HCID 178481995, compound

Product 1

HCID 57378558HCID 57378558, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(4-fluoro-phenyl)-5-(1H-imidazol-4-yl)-1-methyl-1H-[1,2,3]triazole (73 mg, 0.30 mmol), 4-fluoroacetophenone (37 μL, 0.30 mmol) and potassium carbonate (83 mg, 0.60 mmol) in DMF (1.5 mL) was stirred under Ar in a sealed flask and heated at 120° C. for 16 h. After cooling to room temperature the mixture was poured into water and extracted with ethyl acetate and the combined extracts washed with water, brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (51 mg, 47%) as an off white solid after recrystallisation from ethyl acetate. MS: m/e=362.2 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with ethyl acetate
  3. washthe combined extracts washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c0a9179bc79b48ef8f5e150e6d417ee9
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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