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

HRID 518545Notes

Reaction equation

[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:4]([CH3:17])[C:3]1=[O:18].Br[C:20]1[CH:25]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=1[F:30].[F-].[Cs+]>COCCOC.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:30][C:21]1[CH:20]=[CH:25][C:24]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:23][C:22]=1[C:6]1[CH:5]=[C:4]([CH3:17])[C:3](=[O:18])[N:2]([CH3:1])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

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)+

Workup

concentrationThe mixture was concentrated
customthe residue was purified by column chromatography on silica gel (PE: EA=2:1-0:1)

Sources & evidence

ORD record: ord-7bf557bbdd7f40649a5f6ba94a453970
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115114B2

Reaction notes

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