Potassium Acetate → (6-Fluoro-1,3-benzothiazol-7-yl)boronic acid

Participants

Role	Name	HCID	Charge
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	7-Bromo-6-fluorobenzothiazole	HCID 66760448	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(6-Fluoro-1,3-benzothiazol-7-yl)boronic acid	HCID 66760403	71.8%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 7-bromo-6-fluorobenzothiazole (90.7 mg, 0.391 mmol), bis(pinacolato)diboron (149 mg, 0.587 mmol), (1,1′bis-(diphenylphosphino)-ferrocene) palladium dichloride (15.9 mg, 0.0217 mmol), and potassium acetate (76.7 mg, 0.782 mmol) in 1,4-dioxane (1.9 mL) was heated to 85° C. for 24 h. The reaction mixture was concentrated and was then purified by ISCO chromatography (0 to 50% EtOAc:hexane) to give afford 55.3 mg of the title compound as an off-white solid. MS (ESI): 198.02 [M+H]+; HPLC tR=1.18 min (TOF: polar—3 min).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08378104B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-a168ca70a4ae4b12a35c5af2ee5fceea
Source note	uspto-grants-2013_02