Potassium Carbonate → 2-Fluoro-5-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazin-3-yl)benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3-Cyano-4-fluorophenylboronic acid	HCID 2757964	—
Reactant	6-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amine	HCID 86686125	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Fluoro-5-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazin-3-yl)benzonitrile	HCID 67452272	63.2%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of 6-chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amine (5.0 g, 23 mmol, 1.0 equiv) and K2CO3 (9.4 g, 68 mmol, 3.0 equiv) in dioxane (35 mL) was added Pd(dppf)Cl2 (1.7 g, 2.3 mmol, 0.1 equiv) and 3-cyano-4-fluorophenylboronic acid (5.0 g, 30 mmol, 1.3 equiv). The mixture was stirred at 80° C. for 3 hours after which it was allowed to cool to room temperature and concentrated in vacuo. The residue was diluted with EtOAc, washed with saturated NaHCO3, dried over Na2SO4 and evaporated to dryness. The residue was purified by reverse phase HPLC using a CH3CN/water gradient to give the desired product (5.3 g, 63%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08969346B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-82843fa5972f469e8e4de3e70db4038e
Source note	uspto-grants-2015_03