8-Hydroxyquinoline → HCID 24760450, compound

HRID 559571Notes

Reaction equation

HRID 559571 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][NH:7][C:8]([C:10]2[N:11]([CH3:16])[CH:12]=[C:13]([Cl:15])[CH:14]=2)=[O:9])[N:3]=[CH:2]1.I[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]2=[O:30])=[CH:20][CH:19]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:15][C:13]1[CH:14]=[C:10]([C:8]([NH:7][CH2:6][C:4]2[N:3]=[CH:2][N:1]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]4=[O:30])=[CH:20][CH:19]=3)[CH:5]=2)=[O:9])[N:11]([CH3:16])[CH:12]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 18453089HCID 18453089, compoundHCID 178480364HCID 178480364, compound

Product 1

HCID 24760450HCID 24760450, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of N-((1H-imidazol-4-yl)methyl)-4-chloro-1-methyl-1H-pyrrole-2-carboxamide (81 mg, 0.23 mmol), 1-(4-iodophenyl)pyridin-2(1H)-one (100 mg, 0.33 mmol), 8-hydroxyquinoline (15 mg, 0.10 mmol) and K2CO3 (193 mg, 1.40 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (21 mg, 0.11 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the titled compound (25 mg). MS 408.1 and 410.1 (M+H, Cl pattern).

Workup

  1. customwas degassed with Ar
  2. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-e3f586a4246746ac8f3f157e4f2206e8
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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