Dabco → 3-ethylsulfanyl-N-(5-trifluoromethylsulfanylpyridin-2-yl)picolinamide

HRID 713670Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH2:13]([S:15][C:16]1[C:17]([C:22]([NH2:24])=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=1)[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].C1N2CCN(CC2)C1>O.CS(C)=O>[CH2:13]([S:15][C:16]1[C:17]([C:22]([NH:24][C:2]2[CH:7]=[CH:6][C:5]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=2)=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=1)[CH3:14]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 0.64 g of 2-chloro-5-trifluoromethylsulfanylpyridine, 0.54 g of 3-ethylsulfanylpicolinic acid amide, 1.96 g of cesium carbonate, 0.33 g of DABCO and 5 mL of DMSO was stirred at 70° C. for 1 hour. Water was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.40 g of 3-ethylsulfanyl-N-(5-trifluoromethylsulfanylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 48).

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0335cbff07a24aa480734073312bb7fe
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09185910B2

Reaction notes

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