Cesium carbonate → 4-(Trifluoromethyl)-2-(6-(trifluoromethyl)pyridin-3-yloxy)benzonitrile

HRID 538834ノート

反応式

HRID 538834 の反応式
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:14][C:15]([F:24])([F:23])[C:16]1[N:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[F:11][C:10]([F:13])([F:12])[C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:22][C:19]2[CH:20]=[N:21][C:16]([C:15]([F:24])([F:14])[F:23])=[CH:17][CH:18]=2)[CH:9]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrileHCID 27833885-Hydroxy-2-(trifluoromethyl)pyridine

生成物 1

HCID 576877094-(Trifluoromethyl)-2-(6-(trifluoromethyl)pyridin-3-yloxy)benzonitrile収率 87.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-fluoro-4-(trifluoromethyl)benzonitrile (0.19 g, 1.0 mmol), 6-(trifluoromethyl)pyridin-3-ol (0.16 g, 1.0 mmol), and Cs2CO3 (0.33 g, 1 mmol) in DMF (10 mL) was stirred at 60° C. for 18 hours. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine and water, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel with 0-15% ethyl acetate in hexanes to give 4-(trifluoromethyl)-2-(6-(trifluoromethyl)pyridin-3-yloxy)benzonitrile (0.29 g, 87% yield). LC/MS: m/z 333.5 (M+H)+ at 1.83 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel with 0-15% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-bee6dae99c094600bd10d5a929fc1377
出典データセット
uspto-grants-2014_10
特許番号
US08865771B2

反応ノート

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