8-Hydroxyquinoline → HCID 24760755, compound

HRID 559550Notes

Reaction equation

HRID 559550 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=[S:14])=[CH:4][CH:3]=1.[Cl:15][C:16]1[S:20][C:19]([C:21]([NH:23][CH2:24][C:25]2[N:26]=[CH:27][NH:28][CH:29]=2)=[O:22])=[CH:18][CH:17]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:15][C:16]1[S:20][C:19]([C:21]([NH:23][CH2:24][C:25]2[N:26]=[CH:27][N:28]([C:2]3[CH:7]=[CH:6][C:5]([N:8]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]4=[S:14])=[CH:4][CH:3]=3)[CH:29]=2)=[O:22])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 86616333HCID 86616333, compoundHCID 178523075HCID 178523075, compound

Product 1

HCID 24760755HCID 24760755, compound

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-(4-iodophenyl)pyridine-2(1H)-thione prepared above (65 mg, 0.21 mmol), 5-chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 prepared in Example 11 (65 mg, 0.18 mmol), 8-hydroxyquinoline (10 mg, 0.069 mmol) and K2CO3 (75 mg, 0.54 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (27 mg, 0.14 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the title compound (15 mg). MS 427.0 and 429.0 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-2e0af399a2534e38a329689bee1dc796
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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