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

HRID 713670ノート

反応式

HRID 713670 の反応式
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]

参加物

7

反応物 4

HCID 9237DabcoHCID 10796Cesium carbonateHCID 754064102-Chloro-5-((trifluoromethyl)sulfanyl)pyridineHCID 1181133333-Ethylsulfanylpicolinic acid amide

生成物 1

HCID 1182059313-ethylsulfanyl-N-(5-trifluoromethylsulfanylpyridin-2-yl)picolinamide収率 37.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-0335cbff07a24aa480734073312bb7fe
出典データセット
uspto-grants-2015_11
特許番号
US09185910B2

反応ノート

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