8-Hydroxyquinoline → HCID 19370029, compound

HRID 1189501Notes

Reaction equation

HRID 1189501 reaction equation
FC(F)(F)O[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=NC(C3C=CC(C#N)=CC=3)=[N:11]2)=[CH:6][CH:5]=1.N1C=CN=N1.IC1C=CC(OC(F)(F)F)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].O[C:49]1[CH:50]=[CH:51][CH:52]=[C:53]2[C:58]=1[N:57]=[CH:56]C=C2>[Cu]I.CN(C=O)C.O>[C:58]1([N:57]2[CH:56]=[CH:14][N:10]([C:7]3[CH:6]=[CH:5][CH:4]=[CH:9][CH:8]=3)[NH:11]2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

8

Reactant 5

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 27772941-Iodo-4-(trifluoromethoxy)benzeneHCID 669571074-[1-(4-Trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzonitrileHCID 178418936HCID 178418936, compound

Product 1

HCID 19370029HCID 19370029, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

4-[1-(4-Trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzonitrile. The triazole (70 mg, 0.41 mmol), 1-iodo-4-trifluoromethoxybenzene (142 mg, 0.493 mmol), Cs2CO3 (535 mg, 1.644 mmol), CuI (3 mg, 0.012 mmol), 8-hydroxyquinoline (2 mg, 0.012 mmol), and DMF/H2O (2 mL; 10:1 solution) were combined in a 10 mL CEM Microwave reaction vessel fitted with magnetic stir bar and subjected to microwave irradiation at 150° C. for 30 min. The contents were then filtered and concentrated to dryness affording the 1,3-diphenyl triazole intermediate (18 mg, 13%).

Workup

  1. customfitted with magnetic stir bar
  2. customirradiation at 150° C. for 30 min
  3. filtrationThe contents were then filtered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4d7fb1382cb9422eb5cf2de6b1db570b
Source dataset
uspto-grants-2014_03
Patent number
US08674109B2

Reaction notes

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