Pyrazole → ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanoate

HRID 533551ノート

反応式

HRID 533551 の反応式
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)[CH3:2].[NH:23]1[CH:27]=[CH:26][CH:25]=[N:24]1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:21][C:5]([S:17]([CH3:20])(=[O:19])=[O:18])([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:23]2[CH:27]=[CH:26][CH:25]=[N:24]2)=[CH:10][CH:9]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:22]

参加物

6

反応物 3

HCID 1048PyrazoleHCID 1049PyridineHCID 66577887{4-[4-Ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl]phenyl}boronic acid

生成物 1

HCID 66577932ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanoate

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of {4-[4-ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl]phenyl}boronic acid which may be prepared as in Example 10, Step, A (597 mg, 1.82 mmol) in methylene chloride (3 mL) was added pyrazole (62 mg, 0.91 mmol), pyridine (147 uL, 1.82 mmol) and copper (II) acetate (157 mg, 0.866 mmol). The mixture was stirred at ambient temperature under an open atmosphere for 2 days. Silica gel was added, the mixture was concentrated to dryness and purified via silica gel chromatography eluting with ethyl acetate/heptanes to afford ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanoate as an oil. 316.9 mg. LCMS: (M+1) 351.2.

後処理

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated to dryness
  3. custompurified via silica gel chromatography
  4. washeluting with ethyl acetate/heptanes

出典と根拠

ORDレコード
ord-9a0b14b613a64a14941656433d0950fa
出典データセット
uspto-grants-2014_10
特許番号
US08853258B2

反応ノート

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