Ethyl Acetate → {3,5-Dimethyl-1-[4-(4-trifluoromethyl-phenylsulfanylmethyl)-benzyl]-1H-pyrazol-4-yl}-acetic acid methyl ester

HRID 1631928Notes

Reaction equation

HRID 1631928 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][O:19][C:20](=[O:38])[CH2:21][C:22]1[C:23]([CH3:37])=[N:24][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35]Cl)=[CH:31][CH:30]=2)[C:26]=1[CH3:27].C(OCC)(=O)C>CN(C)C=O.O>[CH3:18][O:19][C:20](=[O:38])[CH2:21][C:22]1[C:23]([CH3:37])=[N:24][N:25]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([CH2:35][S:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:8][CH:7]=3)=[CH:33][CH:34]=2)[C:26]=1[CH3:27]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1366534-(Trifluoromethyl)thiophenolHCID 66707535[1-(4-Chloromethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester2×

Product 1

HCID 66707258{3,5-Dimethyl-1-[4-(4-trifluoromethyl-phenylsulfanylmethyl)-benzyl]-1H-pyrazol-4-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4-(Trifluoromethyl)thiophenol (0.25 ml, 1.8 mmol) was dissolved in 5 ml dimethylformamide, and K2CO3 (337 mg, 2.4 mmol) was added to the solution. A solution of [1-(4-chloromethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester (intermediate 16.1.2, 1 g, 1.6 mmol) in dimethylformamide was added to the mixture within 5 min, and the mixture was stirred for 1 h at room temperature. Ethyl acetate and water were added, the mixture was washed with aqueous NaOH solution (1 M) and with water. The organic layer was dried over MgSO4 and the solvent was evaporated under reduced pressure. The residue was purified by MPLC (silica gel, CH2Cl2/methanol 99:1) and preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3).

Workup

  1. washthe mixture was washed with aqueous NaOH solution (1 M) and with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by MPLC (silica gel, CH2Cl2/methanol 99:1) and preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3)

Sources & evidence

ORD record
ord-a04daf9608c745b78dae0962fcfc589d
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

Loading…