Pyrazole → 1-{3-[4-(3,5-Difluorophenoxy)phenoxy]propyl}-1H-pyrazole

HRID 846641Notes

Reaction equation

HRID 846641 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[F:8][C:9]1[CH:10]=[C:11]([CH:24]=[C:25]([F:27])[CH:26]=1)[O:12][C:13]1[CH:23]=[CH:22][C:16]([O:17][CH2:18][CH2:19][CH2:20]Br)=[CH:15][CH:14]=1>CN(C)C=O.C(OCC)(=O)C>[F:8][C:9]1[CH:10]=[C:11]([CH:24]=[C:25]([F:27])[CH:26]=1)[O:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][CH2:20][N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 13455924HCID 13455924, compound

Product 1

HCID 149980181-{3-[4-(3,5-Difluorophenoxy)phenoxy]propyl}-1H-pyrazoleYield 87.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of anhydrous N,N-dimethylformamide (30 ml) and sodium hydride (60% oil suspension; 0.70 g), pyrazole (1.19 g) was added, and the resultant mixture was stirred for 30 minutes. A solution of 3-[4-(3,5-difluorophenoxy)phenoxy]propyl bromide (5.00 g) in anhydrous N,N-dimethylformamide (20 ml) was dropwise added thereto, followed by stirring at room temperature for 5 hours. The reaction mixture was diluted with ethyl acetate (200 ml), washed with a saturated aqueous ammonium chloride solution two times, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily substance thus obtained was subjected to column chromatography to give 4.20 g of 1-{3-[4-(3,5-difluorophenoxy)phenoxy]propyl}pyrazole as a colorless oil. nD23.5 1.5746.

Workup

  1. additionwas added
  2. washwashed with a saturated aqueous ammonium chloride solution two times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe oily substance thus obtained

Sources & evidence

ORD record
ord-4e578ea1bf8e4e6cae3aa2dad783474d
Source dataset
uspto-grants-1992_08
Patent number
US05137907

Reaction notes

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