Dichloromethane → [6-(Dimethylcarbamoyl)pyridin-3-yl]boronic acid

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	5-bromo-N,N-dimethylpicolinamide	HCID 22831618	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
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	[6-(Dimethylcarbamoyl)pyridin-3-yl]boronic acid	HCID 53438177	52.6%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 5-bromo-N,N-dimethylpyridine-2-carboxamide (23 g, 98 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2]bi[[1,3,2]dioxaborolanyl] (27 g, 110 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (4.8 g, 5.9 mmol), 1,1′-bis(diphenylphosphino)ferrocene (3.3 g, 5.9 mmol), and potassium acetate (30 g, 300 mmol) in 1,4-dioxane (600 mL) was heated at 120° C. for 16 h. The mixture was cooled to rt and diluted with EtOAc. The organic solution was washed with saturated ammonium chloride solution which was discarded and then with water (1 L). The water wash was evaporated to give the desired compound (10 g, 50%). LCMS calculated for C8H12BN2O3 (M+H)+: m/z=195.1. found: 195.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09096600B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-f6130e4ef57c4dc38ac59a44c666a420
Source note	uspto-grants-2015_08