1,10-Phenanthroline → HCID 69516007, compound

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate	HCID 22240468	—
Reactant	tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate	HCID 59019959	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 69516007	HCID 69516007	46.2%

Reaction Conditions

Temperature	120 °C

Reaction Steps

Part A. [1-(4-Iodo-phenyl)-cyclopropyl]-carbamic acid tert-butyl ester (0.34 g, 0.95 mmol) and 1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.30 g, 0.97 mmol) were stirred in DMSO (1 mL). K2CO3 (0.25 g, 1.81 mmol), CuI (87 mg, 0.46 mmol) and 1,10-phenanthroline (83 mg, 0.46 mmol) were added. The resulting mixture was heated at 120° C. for 2.5 h. After cooling, it was extracted with EtOAc (2×), washed with H2O and brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by FCC (silica gel, CH2Cl2:EtOAc=1:1, then EtOAc) to give 6-[4-(1-tert-butoxycarbonylamino-cyclopropyl)-phenyl]-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.24 g, yield: 46%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07312214B2
Source dataset	uspto-grants-2007_12
ORD ID	ord-b2edc9aaa12f49dc9fbf5a3bd54c5f93
Source note	uspto-grants-2007_12