8-Hydroxyquinoline → 1-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene

HRID 2357780Notes

Reaction equation

HRID 2357780 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].[OH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]2=[O:10])=[CH:4][C:3]=1[F:9]

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 27370962,5-DiiodofluorobenzeneHCID 178516071HCID 178516071, compound

Product 1

HCID 593866611-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2,5-diiodofluorobenzene II-4 (2.00 g, 5.75 mmol), 2-hydroxypyridine 1-7 (0.546 g, 5.75 mmol), 8-hydroxyquinoline (0.083 g, 0.57 mmol) and K2CO3 (1.00 g, 7.25 mmol) in DMSO (10 mL) was degassed before being charged with CuI (0.109 g, 0.57 mmol). The mixture in a sealed tube was heated at 130° C. overnight. Water and EtOAc were added. The mixture was filtered. The organic layer was separated, then applied to a silica gel column, which was eluted with 0-70% EtOAc in hexane to give 1-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene 3-2 (0.820 g). MS 315.8 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. customThe organic layer was separated
  3. washwas eluted with 0-70% EtOAc in hexane

Sources & evidence

ORD record
ord-415d3155eee1437eb68b3d3e9554fa65
Source dataset
uspto-grants-2010_07
Patent number
US07763608B2

Reaction notes

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