Potassium Carbonate → HCID 66717033, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Methylpyridine-3-Boronic Acid	HCID 2762711	—
Reactant	2-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole	HCID 66221540	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 66717033	HCID 66717033	96.1%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (50 mg, 0.152 mmol), 4-methylpyridine-3-boronic acid (23 mg, 0.167 mmol), PdCl2(dppf) (25 mg, 0.03 mmol) and sat. aq. K2CO3 (0.25 ml) in dioxane (0.5 mL) was heated at 110° C. overnight. The reaction mixture was cooled, diluted with DCM and washed with water. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (MeOH/DCM, 0% to 40%) to give the desired product (50 mg, 96%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.75 min, [M+H]+ m/z 343.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815918B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-6a07928c026648449ea7630128b05fcd
Source note	uspto-grants-2014_08