8-Hydroxyquinoline → HCID 67072314, compound

HRID 1895678Notes

Reaction equation

HRID 1895678 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)(=[O:19])=[O:18].OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[NH4+].[OH-].CCOC(C)=O.[Cu]I>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:23]2[CH:24]=[CH:25][C:20]([S:17]([CH3:16])(=[O:19])=[O:18])=[CH:21][CH:22]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 67072314HCID 67072314, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 4-benzyloxy-2(1H)-pyridone (6.87 g, 34.1 mmol, Aldrich), 4-bromophenyl methyl sulphone (8.01 g, 34.1 mmol, Combi-Blocks Inc.), copper(I) iodide (1.30 g, 6.82 mmol, Aldrich), 8-hydroxyquinoline (0.99 g, 6.82 mmol, Alfa Aesar) and potassium carbonate (6.12 g, 44.3 mmol, EMD) in DMSO (100 mL) was heated at 145° C. for 6 h, cooled to room temperature and then diluted with 10% NH4OH aqueous solution (50 mL) and EtOAc (100 mL). The resulting mixture was filtered and the solid was washed with H2O and EtOAc to give 8.0 g crude product as a greenish solid. MS (ESI) 356 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting mixture was filtered
  3. washthe solid was washed with H2O and EtOAc

Sources & evidence

ORD record
ord-a1da34367b98422b9c5e7fd81c251506
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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