Potassium Acetate → 3-Methoxypyridine-4-boronic acid

Participants

Role	Name	HCID	Charge
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	4-Bromo-3-methoxypyridine hydrochloride	HCID 45789721	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-Methoxypyridine-4-boronic acid	HCID 46739019	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of 4-bromo-3-methoxypyridine hydrochloride (0.34 g, 1.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.13 g, 0.16 mmol), bis(pinacolato)diboron (0.47 g, 1.85 mmol), and potassium acetate (0.75 g, 7.7 mmol) in dry 1,4-dioxane (6.0 mL) was degassed by nitrogen. The mixture was heated to 90° C. After 19 h, the reaction was cooled to rt then filtered. After concentration, the residue was identified as 3-methoxypyridin-4-ylboronic acid that was used without purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08940724B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-f4fad70041ba4349ae22d83393d2a241
Source note	uspto-grants-2015_01