8-Hydroxyquinoline → HCID 24987260, compound

HRID 643013Notes

Reaction equation

HRID 643013 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[N:6][CH:7]=1.[NH:15]1[CH:19]=[C:18]([CH2:20][NH:21][C:22]([C:24]2[S:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[O:23])[N:17]=[CH:16]1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:29][C:26]1[S:25][C:24]([C:22]([NH:21][CH2:20][C:18]2[N:17]=[CH:16][N:15]([C:2]3[CH:7]=[N:6][C:5]([N:8]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]4=[O:14])=[CH:4][CH:3]=3)[CH:19]=2)=[O:23])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 68511944HCID 68511944, compoundHCID 178523075HCID 178523075, compound

Product 1

HCID 24987260HCID 24987260, compoundYield 15.7%

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 1-(5-iodopyridin-2-yl)pyridin-2(1H)-one (75 mg, 0.25 mmol), N-((1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide (60 mg, 0.17 mmol), 8-hydroxyquinoline (10 mg, 0.069 mmol) and K2CO3 (100 mg, 0.72 mmol) in DMSO (1 mL) was degassed with Argon before being charged with CuI (19 mg, 0.10 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the title compound (11 mg). MS found for C19H14ClN5O2S: 412.0 and 414.0 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-aaab1250008b41579aa8a92dafdd2802
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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