8-Hydroxyquinoline → HCID 66969204, compound

HRID 1189495Notes

Reaction equation

HRID 1189495 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[N:3]=[CH:2]1.BrCC(C1C=CC(C#N)=CC=1)=O.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29](I)[CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].OC1C=CC=C2C=1N=CC=C2>[Cu]I.CN(C=O)C.O>[Br:26][C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[C:31]([N:1]2[CH:5]=[C:4]([C:6]3[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=3)[N:3]=[CH:2]2)[CH:32]=1

Participants

8

Reactant 5

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 986544-(Bromoacetyl)benzonitrileHCID 510000714-Bromo-1-chloro-2-iodobenzeneHCID 178509600HCID 178509600, compound

Product 1

HCID 66969204HCID 66969204, compound

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 compound was prepared according to Liu et al. J. Org. Chem. 2005, 70, 10135. 4-(1H-Imidazol-4-yl)-benzonitrile (75 mg, 0.44 mmol; prepared from 4-(2-bromo-acetyl)-benzonitrile using the method of Lynch et al. J. Am. Chem. Soc. 1994, 116, 11030), 4-bromo-1-chloro-2-iodobenzene (169 mg, 0.532 mmol), Cs2CO3 (577 mg, 1.77 mmol), CuI (3 mg, 0.013 mmol), 8-hydroxyquinoline (2 mg, 0.013 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 intermediate 5-bromo-2-chlorophenyl)-1H-imidazol-4-yl]-benzonitrile (68 mg, 43%).

Workup

  1. customThe compound was prepared
  2. customfitted with magnetic stir bar
  3. customirradiation at 150° C. for 30 min
  4. filtrationThe contents were then filtered
  5. concentrationconcentrated to dryness
  6. customaffording intermediate 5-bromo-2-chlorophenyl)-1H-imidazol-4-yl]-benzonitrile (68 mg, 43%)

Sources & evidence

ORD record
ord-b7257fe353b94c66bc708b009f30f804
Source dataset
uspto-grants-2014_03
Patent number
US08674109B2

Reaction notes

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