8-Hydroxyquinoline → HCID 178474185, compound

HRID 1802620Notes

Reaction equation

HRID 1802620 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](=[O:17])[CH3:16])=[CH:4][CH:3]=1.[Cl:18][C:19]1[S:23][C:22]([C:24]([NH:26][CH2:27][C:28]2[N:29]=[CH:30][NH:31][CH:32]=2)=[O:25])=[CH:21][CH:20]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[C:15](/[N:14]=[C:9]1/[N:8]([C:5]2[CH:6]=[CH:7][C:2]([N:31]3[CH:32]=[C:28]([CH2:27][NH:26][C:24]([C:22]4[S:23][C:19]([Cl:18])=[CH:20][CH:21]=4)=[O:25])[N:29]=[CH:30]3)=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=[CH:10]/1)(=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 178474184HCID 178474184, compoundHCID 178523075HCID 178523075, compound

Product 1

HCID 178474185HCID 178474185, compoundYield 6.6%

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)acetamide (120 mg, 0.27 mmol), 5-Chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 (109 mg, 0.30 mmol), 8-hydroxyquinoline (15 mg, 0.10 mmol) and K2CO3 (100 mg, 0.72 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (24 mg, 0.12 mmol). The mixture in a sealed tube was heated at 130° C. for 5 h. It was then purified by HPLC to give the titled compound (8 mg). MS 452.0 and 454.0 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-e5ae877a88d845348ff555e29112547c
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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