Imidazole → 2-(1H-Imidazol-1-yl)pyridine-4-carboxylic acid

Participants

Role	Name	HCID	Charge
Reactant	Imidazole	HCID 795	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Bromoisonicotinic acid	HCID 222701	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	2-(1H-Imidazol-1-yl)pyridine-4-carboxylic acid	HCID 26967253	108%

Reaction Conditions

Temperature	125 °C

Reaction Steps

To a solution of 2-bromoisonicotinic acid (1.87 g, 9.26 mmol), 1H-imidazole (573 mg, 8.42 mmol) and Cs2CO3 (6.03 g, 18.5 mmol) in DMSO (18.6 mL), was added CuI (176 mg, 0.926 mmol). The mixture was heated to 125° C., stirred for 18 hours, cooled to room temperature, filtered and purified by preparative HPLC (10-90% acetonitrile in water) to give the title compound as a light pink solid (1.72 g, 98%). MS 190 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08877922B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-4b279022d76741a68a097faa322c3cbd
Source note	uspto-grants-2014_11