8-Hydroxyquinoline → HCID 24986896, compound

HRID 642993Notes

Reaction equation

HRID 642993 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=3)[N:14]([CH3:16])[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[OH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([N:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]4=[O:24])=[CH:19][CH:18]=3)[N:14]([CH3:16])[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 59260114HCID 59260114, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 24986896HCID 24986896, 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 5-chloro-N-((2-(4-iodophenyl)-1-methyl-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide prepared above (14 mg, 0.031 mmol), 2-hydroxypyridine (14 mg, 0.15 mmol), 8-hydroxyquinoline (14 mg, 0.097 mmol) and K2CO3 (30 mg, 0.22 mmol) in DMSO (0.5 mL) was degassed with Argon before being charged with CuI (9 mg, 0.047 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the titled compound (2 mg). MS 425.1 and 427.1 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-f7df8b38ed774fb5b660f1cea8e8dc50
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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