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

HRID 2177680
ノート
印刷プレビュー

反応式

HRID 2177680 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1048PyrazoleHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 529139736-(Benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 14829
Copper oxide
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-ead8a9b0ec9f49558567e55a8f140671
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09067905B2

反応ノート

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