Dichloromethane → 5-(5-phenyl-1,3,4-thiadiazol-2-yl)-1-tosyl-1H-indol-3-ylboronic acid

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole	HCID 68328784	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5-(5-phenyl-1,3,4-thiadiazol-2-yl)-1-tosyl-1H-indol-3-ylboronic acid	HCID 68328668	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

In a 20 mL microwave tube, a mixture of 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (493 mg, 0.884 mmol), bis(pinacolato)diboron (674 mg, 2.65 mmol), potassium acetate (434 mg, 4.42 mmol), PdCl2(dppf), complex with DCM (108 mg, 0.133 mmol) and DMF (4.0 mL) was stirred at 90° C. in the oil bath for 1 h. The mixture was treated with H2O, extracted with EtOAc (50 mL) and washed with brine (2×20 mL), dried over MgSO4, filtered and concentrated affording a brown oil which crystallized upon standing. It was used in the next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09321756B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-1f4b2f7b03864c17ab84222a8e946055
Source note	uspto-grants-2016_04