Sodium Carbonate → 6-Phenylpyridazin-3-amine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	6-Amino-3-chloropyridazine	HCID 21643	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-Phenylpyridazin-3-amine	HCID 11958915	78.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 6-chloropyridazin-3-amine (2 g, 15.4 mmol), phenylboronic acid (2.83 g, 23.2 mmol), Pd2(dba)3 (0.89 g, 1.6 mmol), X-phos (2.94 g, 6.2 mmol) and Na2CO3 (4.91 g, 46.3 mmol) in dioxane (50 mL) and water (5 mL) was heated to 100° C. with stirring for 6 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=20:1) to give 6-phenylpyridazin-3-amine (2.06 g, 78%) as a white solid. LC-MS: [M+H]+, 172.1, tR=1.04 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09169259B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-d731929ecbb94247a898a7505ec170e6
Source note	uspto-grants-2015_10