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Pyrazole → 6-(Benzenesulphonylmethyl)-2-methoxy-3-(pyrazol-1-yl)benzoic acid

HRID 2177680
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HRID 2177680 반응식
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:20][CH3:21])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:29]1[CH:33]=[CH:32][CH:31]=[N:30]1.C(OCC)(=O)C>CN(C=O)C.[Cu]=O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:20][CH3:21])[C:14]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1048PyrazoleHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 529139736-(Benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid2회

생성물 1

HCID 529130506-(Benzenesulphonylmethyl)-2-methoxy-3-(pyrazol-1-yl)benzoic acid수율 26.9%

시약·촉매·용매 2

HCID 14829
Copper oxide
촉매
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid (Intermediate 133, 0.1 g), copper (II) oxide (0.004 g), cesium carbonate (0.254 g) and pyrazole (0.018 g) in DMF (2 ml) was sealed in a microwave vial in an atmosphere of nitrogen and heated at 100° C. for 18 hours. After cooling, ethyl acetate was added, and the mixture was filtered through celite. The filtrate was evaporated to dryness and the residue was purified by HPLC, eluting with a mixture of acetonitrile and water containing 0.1% formic acid with a gradient of 40-60% to give 6-(benzenesulphonylmethyl)-2-methoxy-3-(pyrazol-1-yl)benzoic acid (0.026 g) as a white solid.

후처리

  1. customwas sealed in a microwave vial in an atmosphere of nitrogen
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through celite
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by HPLC
  6. washeluting with a mixture of acetonitrile and water containing 0.1% formic acid with a gradient of 40-60%

출처 및 근거

ORD 기록
ord-ead8a9b0ec9f49558567e55a8f140671
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067905B2

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