Sodium Iodide → 4-Iodo-1-(4-fluorophenyl)indazole

Participants

Role	Name	HCID	Charge
Reactant	Sodium Iodide	HCID 5238	—
Reactant	1-N,2-N-dimethylcyclohexane-1,2-diamine	HCID 551074	—
Reactant	4-Bromo-1-(4-fluorophenyl)-1H-indazole	HCID 66687100	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-Iodo-1-(4-fluorophenyl)indazole	HCID 66687817	98%

Reaction Conditions

Temperature	110 °C

Reaction Steps

4-Bromo-1-(4-fluorophenyl)indazole (291 mg, 1 mmol), copper(I)iodide (9.5 mg, 0.05 mmol), sodium iodide (300 mg, 2 mmol) and (1R,2R)—(N,N′-dimethylcyclohexane-1,2-diamine (14.2 mg, 0.1 mmol) in dioxane (1 ml) were mixed and stirred in argon at 110° C. All starting material was consumed after 24 h. The mixture was cooled and ammonia (5 ml, 28% in water) and water (20 ml) were added followed by extraction with DCM (2×15 ml). The organic phase was concentrated and the crude product was purified by flash chromatography (EtOAc/Heptane) to give the title compound (322 mg, 98%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08030340B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-c8f3d2efad864d6685702790564b0b14
Source note	uspto-grants-2011_10