Sodium Carbonate → 6-fluoro-1'-methyl-[3,4'-bipyridin]-2'(1'H)-one

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Fluoropyridine-5-boronic acid pinacol ester	HCID 12177222	—
Reactant	4-Bromo-1-methylpyridin-2(1H)-one	HCID 22132396	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	6-fluoro-1'-methyl-[3,4'-bipyridin]-2'(1'H)-one	HCID 118046548	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (500 mg, 2.242 mmol) was added PdCl2(dppf) (68.3 mg, 0.093 mmol), 4-bromo-1-methylpyridin-2(1H)-one (351 mg, 1.868 mmol), 2M Na2CO3 (4.1 mL) and DME (8.3 mL) at room temperature. The reaction mixture was heated at microwave synthesizer for 10 min at 120° C. The reaction mixture was extracted with EtOAc. The organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered off, and concentrated in vacuo. The crude 6-fluoro-1′-methyl-[3,4′-bipyridin]-2′(1′H)-one was purified by flash chromatography (gradient EtOAc in DCM). LCMS (m/z): 205.2 (MH+), 0.47 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09242996B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-086f88ad15cf4748a40b4eb22b45651c
Source note	uspto-grants-2016_01