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

HRID 1861595Notes

Reaction equation

HRID 1861595 reaction equation
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

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydride2×HCID 86758877HCID 86758877, compoundHCID 178429419HCID 178429419, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22335286Ethyl acetate pentaneSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-78413f2dcc634a48a9be8c52de2fb8a5
Source dataset
uspto-grants-2003_03
Patent number
US06534447B1

Reaction notes

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