1,10-Phenanthroline → Methyl 3-{[2-(4-amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}benzoate

https://huagongshe.com/reaction/1986370

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Methyl 3-Hydroxybenzoate	HCID 88068	—
Reactant	4-(6-Bromo-1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)-furazan-3-amine	HCID 86623348	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Methyl 3-{[2-(4-amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}benzoate	HCID 11304916	33%

Reaction Conditions

Temperature	125 °C

Reaction Steps

A heterogeneous mixture of the product from Step 7 (0.75 g, 2.1 mmol), methyl 3-hydroxybenzoate (1.5 equiv), 1,10-phenanthroline (1.5 equiv), copper (I) iodide (0.42 g, 2.2 mmol) and cesium carbonate (1.44 g, 3.78 mmol) in toluene (30 mL) and ethyl acetate (1.5 mL) was heated in a sealed tube at 125° C. for 2 days. The reaction mixture was cooled to rt triturated with ethyl acetate. The resulting crude solid was crystallized from ethanol to afford the title compound (0.30 g, 33%). MS (ES+) m/e 429 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07547779B2
Source dataset	uspto-grants-2009_06
ORD ID	ord-2979f75db831494eb35b0342a77cbe01
Source note	uspto-grants-2009_06