8-Hydroxyquinoline → HCID 178492113, compound

HRID 499804Notes

Reaction equation

HRID 499804 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10]/[C:9]/2=[N:14]\[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[Cl:23][C:24]1[S:28][C:27]([C:29]([NH:31][CH2:32][C:33]2[N:34]=[CH:35][NH:36][CH:37]=2)=[O:30])=[CH:26][CH:25]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:23][C:24]1[S:28][C:27]([C:29]([NH:31][CH2:32][C:33]2[N:34]=[CH:35][N:36]([C:2]3[CH:7]=[CH:6][C:5]([N:8]4[CH:13]=[CH:12][CH:11]=[CH:10]/[C:9]/4=[N:14]\[C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)=[CH:4][CH:3]=3)[CH:37]=2)=[O:30])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 178492112HCID 178492112, compoundHCID 178523075HCID 178523075, compound

Product 1

HCID 178492113HCID 178492113, compoundYield 28.5%

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 (E)-N-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)-4-methoxybenzenamine (90 mg, 0.17 mmol), 5-Chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 (62 mg, 0.17 mmol), 8-hydroxyquinoline (14 mg, 0.096 mmol) and K2CO3 (100 mg, 0.72 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (20 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 titled compound (25 mg). MS 516.0 and 518.1 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-33a846e41df648efa5c1d0b102339b45
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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