1,10-Phenanthroline → 3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenol

https://huagongshe.com/reaction/1986374

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3-[(Tert-butyldimethylsilyl)oxy]phenol	HCID 11447440	—
Reactant	4-(6-Bromo-1-Ethyl-1h-Imidazo[4,5-C]pyridin-2-Yl)-1,2,5-Oxadiazol-3-Amine	HCID 16099851	—
Solvent	Toluene	HCID 1140	—
Product	3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenol	HCID 11371157	7%

Reaction Conditions

Temperature	120 °C

Reaction Steps

The product from Step 1 (46 mg, 0.20 mmol) in toluene (10 mL) was treated with the product from Step 2 (42 mg, 0.14 mmol), cuprous iodide (26 mg, 0.14 mmol), 1,10-phenanthroline (43 mg, 0.24 mmol), and cesium carbonate (88 mg, 0.27 mmol). The resulting mixture was heated to 120° C. for 48 hours in a sealed tube. After concentration the residue was purified by reverse phase HPLC to give the title compound (3.3 mg, 7%). MS (ES+) m/e 339 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07547779B2
Source dataset	uspto-grants-2009_06
ORD ID	ord-e1cbc58a817a4abe81eebe57cd48ce10
Source note	uspto-grants-2009_06