8-Hydroxyquinoline → HCID 66974111, compound

HRID 559544Notes

Reaction equation

HRID 559544 reaction equation
I[C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH:18][CH2:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[OH:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([C:2]2[CH:10]=[CH:9][C:8]([N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]3=[O:17])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:24]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 66974180HCID 66974180, compoundHCID 178519868HCID 178519868, compound

Product 1

HCID 66974111HCID 66974111, 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 2-iodo-5-(2-oxopyridin-1(2H)-yl)benzoic acid prepared above (220 mg, 0.65 mmol), 4-hydroxymethylimidazole II-1 (126 mg, 1.29 mmol), 8-hydroxyquinoline (19 mg, 0.13 mmol) and K2CO3 (290 mg, 2.10 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (25 mg, 0.13 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give 2-(4-(hydroxymethyl)-1H-imidazol-1-yl)-5-(2-oxopyridin-1(2H)-yl)benzoic acid (92 mg). MS 312.1 (M+H).

Workup

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

Sources & evidence

ORD record
ord-95c3acf760564b8d9894100a8714674d
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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