N-methyl-2-pyrrolidone → 2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(3-trifluoromethylthioprop-2-enyloxy)pyridine

HRID 1861595ノート

反応式

HRID 1861595 の反応式
Br[CH2:2][CH:3]=[CH:4][S:5][C:6]([F:9])([F:8])[F:7].[OH:10][C:11]1[N:16]=[C:15]([O:17][C:18]2[N:22]([CH3:23])[N:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH:14]=[C:13]([CH3:28])[CH:12]=1.[H-].[Na+].CN1CCCC1=O>CCCCC.C(OCC)(=O)C.CN(C=O)C>[CH3:23][N:22]1[C:18]([O:17][C:15]2[CH:14]=[C:13]([CH3:28])[CH:12]=[C:11]([O:10][CH2:2][CH:3]=[CH:4][S:5][C:6]([F:9])([F:8])[F:7])[N:16]=2)=[CH:19][C:20]([C:24]([F:27])([F:26])[F:25])=[N:21]1

参加物

7

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydride2 回HCID 867588771-Bromo-3-(trifluoromethylthio)-prop-2-eneHCID 178429419HCID 178429419、化合物

生成物 1

HCID 734539702-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(3-trifluoromethylthioprop-2-enyloxy)pyridine収率 18.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 22335286Ethyl acetate pentane溶媒

反応条件

温度
120 °C

実験手順

1-Bromo-3-(trifluoromethylthio)-prop-2-ene (1.05 g, Example B) is added to a mixture of 1A (1.08 g), sodium hydride (60% in oil, 0.18 g) and N-methylpyrrolidone (20 ml) and DMF (1 ml). The reaction mixture is stirred for 6 hours at 120° C. The remaining sodium hydride is deactivated and the resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 10/1 v/v) yields 0.3 g of the title compound.

後処理

  1. filtrationfiltered through a bed of silica gel
  2. washThe filtrate is washed with water
  3. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 10/1 v/v)

出典と根拠

ORDレコード
ord-78413f2dcc634a48a9be8c52de2fb8a5
出典データセット
uspto-grants-2003_03
特許番号
US06534447B1

反応ノート

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