Water → HCID 18409465, compound

HRID 993319Notes

Reaction equation

HRID 993319 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([OH:23])=[N:10][NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1.O>CN(C=O)C>[F:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][O:23][C:9]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[NH:11][N:10]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 178504700HCID 178504700, compound

Product 1

HCID 18409465HCID 18409465, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-(4-fluorophenyl)-3-hydroxy-5-(4-(methylsulphonyl)phenyl)-pyrazole [(366 mg, 1.1 mmol), prepared according to the method of Example 5C, K2CO3 (152 mg, 1.1 mmol) in DMF (20 mL) at 50° C. was treated dropwise with a solution of 1-(bromomethyl)-4-fluorobenzene (0.141 mL, 1.1 mmol) in DMF (5 mL), and the mixture was stirred for 45 minutes. The reaction mixture was then poured into water and extracted with ethyl acetate. The acetate extract was washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed (silica gel, 1:1 hexanes-ethyl acetate) to provide 3-(4-fluorobenzyloxy)-4-(4-fluorophenyl)-5-(4-(methyl-sulphonyl)phenyl)pyrazole (yield: 325 mg; 80%). MS (APCI+) m/z 441 (M+H)+; (APCI−) m/z 475 (M+Cl)−; 1H NMR (300 MHz, DMSO-d6) δ3.26 (s, 3H), 5.28 (s, 2H), 7.19 (m, 3H), 7.25 (m, 3H), 7.48 (m, 2H), 7.57 (d, J=9 Hz, 2H), 7.94 (d, J=9 Hz, 2H).

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. extractionThe acetate extract
  4. washwas washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (silica gel, 1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-efba09d6259e4e778e2d049d792ea12c
Source dataset
uspto-grants-2002_10
Patent number
US06472416B1

Reaction notes

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