8-Hydroxyquinoline → 1-(4-iodophenyl)-2-methyl-1H-imidazole-4-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	8-Hydroxyquinoline	HCID 1923	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	p-Diiodobenzene	HCID 12208	—
Reactant	HCID 178418999	HCID 178418999	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(4-iodophenyl)-2-methyl-1H-imidazole-4-carbaldehyde	HCID 59386658	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

The mixture of 1,4-diiodobenzene 1-1 (600 mg, 1.8 mmol), 2-methyl-1H-imidazole-4-carbaldehyde (200 mg, 1.8 mmol), K2CO3 (503 mg, 3.6 mmol), CuI (105 mg, 0.55 mmol) and 8-hydroxyquinoline (80 mg, 0.55 mol) in 5 mL DMSO and 5 mL dioxane in a sealed tube was stirred for 2 days at 120° C. It was cooled to rt, and to it was added 60 mL water. The mixture was stirred for 30 min and filtered through a celite layer. The filtrate was concentrated in vacuo and subjected to reverse phase preparative HPLC to isolate 1-(4-iodophenyl)-2-methyl-1H-imidazole-4-carbaldehyde 5-1. MS found for C11H9IN2O (M+H)+313.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08063077B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-d97fc436d21c4e01a965fa5471e02b08
Source note	uspto-grants-2011_11