Imidazole → 1-{3-(4-Fluorophenyl)-trans-3-[6-(4-fluorophenoxymethyl)tetrahydropyran-2-yloxy]propyl}imidazole

HRID 905086Notes

Reaction equation

HRID 905086 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[F:8][C:9]1[CH:34]=[CH:33][C:12]([O:13][CH2:14][C@@H:15]2[O:20][C@@H:19]([O:21][CH:22]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:23][CH2:24]Cl)[CH2:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1>CN(C)C=O>[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH:22]([O:21][C@H:19]2[CH2:18][CH2:17][CH2:16][C@H:15]([CH2:14][O:13][C:12]3[CH:33]=[CH:34][C:9]([F:8])=[CH:10][CH:11]=3)[O:20]2)[CH2:23][CH2:24][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 54428102Trans-6-(4-fluorophenoxymethyl)-2-[3-chloro-1-(4-fluorophenyl)propoxy]tetrahydropyran

Product 1

HCID 543473471-{3-(4-Fluorophenyl)-trans-3-[6-(4-fluorophenoxymethyl)tetrahydropyran-2-yloxy]propyl}imidazoleYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 56 mg of imidazole and 36 mg of 55% sodium hydride was stirred in 2 ml of dimethylformamide at 60°-70° C. for 30 minutes. The mixture was left to cool at room temperature, and then a solution of 218 mg of trans-6-(4-fluorophenoxymethyl)-2-[3-chloro-1-(4-fluorophenyl)propoxy]tetrahydropyran in 1 ml of dimethylformamide was added, and the mixture was heated, with stirring, at 80°-90° C. for 6 hours. At the end of this time, the mixture was treated and the product purified essentially as described in Example 34(b)(i), to give 110 mg of the title compound.

Workup

  1. waitThe mixture was left
  2. temperaturethe mixture was heated
  3. additionAt the end of this time, the mixture was treated
  4. customthe product purified essentially

Sources & evidence

ORD record
ord-f312534bff594adfa4a10f5d0d3d3a98
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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