Potassium Carbonate → HCID 86700371, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2,6-Dibromopyridine	HCID 12274	—
Reactant	1-Methyl-1H-indazole-5-boronic acid	HCID 22558910	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 86700371	HCID 86700371	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

In a 10-20 mL reaction vial, the 1-methyl-1H-indazol-5-ylboronic acid (500 mg, 2.73 mmol) and the 2,6-dibromopyridine (776 mg, 3.27 mmol) were dissolved in dioxane (7 mL) under argon atmosphere. The mixture was bubbled with argon for 5 min and then potassium carbonate (754 mg, 5.46 mmol) and PdCl2(dppf) catalyst were added sequentially. The resulting reaction mixture was then sealed and heated in oil bath at 110° C. for 3 h. Reaction was then diluted with EtOAc (10 mL), filtered and the filtrate was collected and concentrated. Residue was purified on silica gel column with 0-25% EtOAc/Hex to afford the title product. LCMS-ESI+: calc'd for: C13H10BrN3: 288.0, 290.0 (M+H+); Found: 288.2, 290.3 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987250B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-9bd0ba3cebec4360a58825856400a8d6
Source note	uspto-grants-2015_03