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

HRID 225733ノート

反応式

HRID 225733 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

In a glass tube was added successively 0.29 mmol 2-Iodo-5-methanesulfonyl-benzoic acid methyl ester (example B19(c)), 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 (degassed). 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 log Flashpack cartridge. Eluent: Heptane/ethylacetate to provide the title compound (57%) as a light yellow oil. MS (m/e): 295.0([M+H]+, 100%).

後処理

  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 log Flashpack cartridge

出典と根拠

ORDレコード
ord-1dd931991a4c4604899cbe2ee2bfb89c
出典データセット
uspto-grants-2009_07
特許番号
US07557114B2

反応ノート

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