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

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Sodium Sulfate	HCID 24436	—
Reactant	2-Fluoropyridine-5-boronic acid pinacol ester	HCID 12177222	—
Reactant	5-Bromo-1((2-(trimethylsilyl)ethoxy)methyl)pyridin-2(1H)-one	HCID 123359998	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	6'-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-[3,3'-bipyridin]-6(1H)-one	HCID 124024042	52%

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)pyridin-2(1H)-one (568 mg, 1.868 mmol) in DME (6227 μL, Ratio: 2.000) was added PdCl2(dppf) (68.3 mg, 0.093 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (500 mg, 2.242 mmol), 2M Na2CO3 (3113 μl, Ratio: 1.000) at room temperature. The reaction mixture was heated at microwave synthesizer for 10 min at 120° C. To the reaction mixture, sodium sulfate and EtOAc were added. After filtered off, the volatile materials were removed in vacuo. The crude product was purified by flash chromatography (gradient EtOAc in heptane) yielding 6′-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-[3,3′-bipyridin]-6(1H)-one (52%). LCMS (m/z): 321.3 (MH+), 0.93 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09242996B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-9c7dbe57e6ab4bdf96159fb22ab89964
Source note	uspto-grants-2016_01