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

HRID 1861595노트

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HRID 1861595 반응식
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

참가 물질

7

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydride2회HCID 867588771-Bromo-3-(trifluoromethylthio)-prop-2-eneHCID 178429419HCID 178429419, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 22335286Ethyl acetate pentane용매

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-78413f2dcc634a48a9be8c52de2fb8a5
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534447B1

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