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

HRID 533551노트

반응식

HRID 533551 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9a0b14b613a64a14941656433d0950fa
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853258B2

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