3,6-Dichloropyridazine → 3-Chloro-6-(2-fluoro-4-methyl-phenyl)-pyridazine

Participants

Role	Name	HCID	Charge
Reactant	3,6-Dichloropyridazine	HCID 67331	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	Potassium Fluoride	HCID 522689	—
Reactant	(2-Fluoro-4-methylphenyl)boronic acid	HCID 2783132	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-Chloro-6-(2-fluoro-4-methyl-phenyl)-pyridazine	HCID 11665739	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of 3,6-dichloropyridazine (2.0 g, 13.42 mmole) in 1,4-dioxane (20 ml) are added Pd2(dba)3 (0.21 g, 0.2 mmole), P(tBu)3 (0.122 g, 0.6 mmole) in 1,4-dioxane (1 ml), KF (2.57 g, 44.3 mmole) and 2-fluoro-4-methylbenzeneboronic acid (step 31.1, 2.68 g, 17.45 mmole). The resulting mixture is heated at 120° C. for 48 h. The reaction mixture is filtered through celite and washed pad with EtOAc. The filtrate is washed with H2O, dried over MgSO4 (anhydrous) and evaporated under reduced pressure to give a brown solid, which is purified by chromatography, affording the title product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08236803B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-25d77c4399fc4f3ca3ad29b581211f52
Source note	uspto-grants-2012_08