Potassium Carbonate → 6-(5-Bromo-2-fluorophenyl)-1,2,4-triazin-3-amine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(5-Bromo-2-fluorophenyl)boronic acid	HCID 10856974	—
Reactant	6-Bromo-1,2,4-triazin-3-amine	HCID 15332564	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-(5-Bromo-2-fluorophenyl)-1,2,4-triazin-3-amine	HCID 67453464	41%

Reaction Conditions

Temperature	90 °C

Reaction Steps

6-Bromo-1,2,4-triazin-3-amine (9.1 g, 40.8 mmol), 5-bromo-2-fluorophenylboronic acid (98.9 g, 40.8 mmol), (dppf)PdCl2 (3.0 g, 4.0 mmol), nitrogen-sparged dioxane (81.6 mL), and aq. 2 N K2CO3 (17 mL) were combined and heated in a round bottom flask at 90° C. for 4 h. The hot mixture was filtered through a pad of celite and diluted with EtOAc and washed with water. Concentration followed by trituration with DCM afforded a tan solid (4.5 g), m/z=269.0 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133123B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-ed26deeb77da45faa742c0064f9851bd
Source note	uspto-grants-2015_09