4-Methylpyrazole → 5-Methanesulfonyl-2-(4-methyl-pyrazol-1-yl)-benzoic acid methyl ester

HRID 552684Notes

Reaction equation

HRID 552684 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1I.[CH3:16][C:17]1[CH:18]=[N:19][NH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.[Cu]I.O.ClCCl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:19]1[CH:18]=[C:17]([CH3:16])[CH:21]=[N:20]1

Participants

9

Reactant 4

HCID 34064-MethylpyrazoleHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 59853752Methyl 2-iodo-5-(methylsulfonyl)benzoate

Product 1

HCID 577533435-Methanesulfonyl-2-(4-methyl-pyrazol-1-yl)-benzoic acid methyl esterYield 57%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

In a glass tube was added successively 0.29 mmol 2-Iodo-5-methanesulfonyl-benzoic acid methyl ester (CAS: 847547-09-5), 0.35 mmol 4-methylpyrazole, 0.59 mmol potassium carbonate, 0.06 mmol CuI and a solution of 0.12 mmol trans-1,2-diaminocyclohexane in 0.4 ml dioxane (degased). The tube was filled with argon and sealed with a cap. The reaction mixture was heated at 120° C. overnight. The reaction mixture was cooled down to room temperature, dichloromethane and water were added. The aqueous phase was extracted 2 times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The crude compound was purified on a 10 g Flashpack cartridge. Eluent: Heptane/ethylacetate to provide the title compound (57%) as a light yellow oil. MS (m/e): 295.0([M+H]+, 100%).

Workup

  1. additionThe tube was filled with argon
  2. customsealed with a cap
  3. temperatureThe reaction mixture was cooled down to room temperature
  4. extractionThe aqueous phase was extracted 2 times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated
  7. customThe crude compound was purified on a 10 g Flashpack cartridge

Sources & evidence

ORD record
ord-7ab6f579003549188a6f69d80678f9d1
Source dataset
uspto-grants-2011_05
Patent number
US07951836B2

Reaction notes

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