Cesium fluoride → 5-(2-Fluoro-5-methylsulfonylphenyl)-1,3-dimethylpyridin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium fluoride	HCID 25953	—
Reactant	2-Bromo-1-fluoro-4-(methylsulfonyl)benzene	HCID 67387081	—
Reactant	1,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-one	HCID 71270309	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Methanol	HCID 887	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	5-(2-Fluoro-5-methylsulfonylphenyl)-1,3-dimethylpyridin-2-one	HCID 118022596	61%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (2.50 g, 10.0 mmol), 2-bromo-1-fluoro-4-methylsulfonylbenzene (2.54 g, 10.0 mmol), CsF (3.8 g, 25.0 mmol), Pd(dppf)Cl2 (0.73 g, 1.0 mmol) in DME (50 mL) and MeOH (25 ml) was stirred at 80° C. for 18 hrs under N2. The mixture was concentrated and the residue was purified by column chromatography on silica gel (PE:EA=2:1-0:1) to give the title compound (1.8 g, 61%) as a red solid. LCMS: 295.9 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034900B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-4cb4be705a7c4136a38a01f57919850b
Source note	uspto-grants-2015_05