8-Hydroxyquinoline → 1-(5-Fluoropyridin-2-yl)-1H-imidazo[4,5-c]pyridine

HRID 2177546Notes

Reaction equation

HRID 2177546 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O.[Cu-]=O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:5]3[CH:6]=[CH:7][N:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)=[N:12][CH:13]=1

Participants

8

Reactant 4

HCID 19238-HydroxyquinolineHCID 92271H-Imidazo(4,5-c)pyridineHCID 10796Cesium carbonateHCID 27831712-Bromo-5-fluoropyridine

Product 1

HCID 904095831-(5-Fluoropyridin-2-yl)-1H-imidazo[4,5-c]pyridineYield 25%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 5-azabenzimidazole (1.00 g, 8.40 mmol), 2-bromo-5-fluoropyridine (1.48 g, 8.40 mmol), copper (I) oxide (0.13 g, 0.84 mmol), 8-hydroxyquinoline (0.24 g, 1.68 mmol), and Cs2CO3 (5.47 g, 16.8 mmol) in DMSO (4 mL) was irradiated in a microwave apparatus for 1 hour at 140° C. The reaction was diluted with H2O (100 mL) and extracted with EtOAc (75 mL×3). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; MeOH(NH3):DCM) gave the title compound (0.45 g, 25%). MS (ESI): mass calculated for C11H7FN4, 214.07. m/z found 215.1 [M+H]+.

Workup

  1. extractionextracted with EtOAc (75 mL×3)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3c780160838043d7b5bf387aff1c74a7
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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