Potassium Carbonate → HCID 59380310, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	3-Fluorophenylboronic acid	HCID 2733986	—
Reactant	3-Bromo-6-chloroimidazo(1,2-b)pyridazine	HCID 12872323	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 59380310	HCID 59380310	61.8%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (500 mg, 2.15 mmol) in a mixed solvent of dioxane (5 mL) and water (0.5 mL) was added (3-fluorophenyl)boronic acid (273 mg, 1.96 mmol), K2CO3 (811 mg, 5.88 mmol) and Pd(dppf)2Cl2 (79 mg, 0.098 mmol). The reaction mixture was stirred at 80° C. overnight under N2. TLC (PE:EA=5:1) showed the starting material was consumed. The mixture was cooled and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=20:1 to 1:1) to give 6-chloro-3-(3-fluorophenyl)imidazo[1,2-b]pyridazine (300 mg, 56%) as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09416132B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-012fe408cb684072a2d63e0ed2e23772
Source note	uspto-grants-2016_08