8-Hydroxyquinoline → HCID 19370029, compound

HRID 708949Notes

Reaction equation

HRID 708949 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.I[C:7]1[CH:12]=[CH:11][C:10](OC(F)(F)F)=[CH:9][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].O[C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:34]=1N=CC=C2>[Cu]I.CN(C=O)C.O>[C:7]1([N:1]2[CH:5]=[CH:4][N:3]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:34]=3)[NH:2]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 27772941-Iodo-4-(trifluoromethoxy)benzeneHCID 178418936HCID 178418936, compound

Product 1

HCID 19370029HCID 19370029, compoundYield 671.8%

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

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-91077264812548e388585f03a9874937
Source dataset
uspto-grants-2015_11
Patent number
US09179681B2

Reaction notes

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