Toluene → 6-cyclopropyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

HRID 74459

反応式

HRID 74459 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9](Br)[CH:8]=2)=[O:4].[CH3:25][C:26](P(C(C)(C)C)C1C=CC=CC=1)([CH3:28])C.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([CH:28]1[CH2:26][CH2:25]1)[CH:8]=2)=[O:4]

参加物

8

反応物 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 316378Di-tert-butylphenylphosphineHCID 680048106-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

生成物 1

HCID 680048306-cyclopropyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Predetermined amounts of 6-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester (300 mg, 0.73 mmol), palladium acetate (16.5 mg, 0.07 mmol), bis(1,1-dimethylethyl)phenylphosphine (0.028 ml, 0.12 mmol), potassium cyclopropyl trifluoroborate (163 mg, 1.1 mmol), and cesium carbonate (718 mg, 2.2 mmol) were placed in a reaction container, and toluene (5 ml) and water (0.5 ml) were added thereto. The resulting mixture was then stirred at 100° C. for 14 hours. After cooling it to room temperature, the mixture was diluted with ethyl acetate, and washed twice with water, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate=97/3 to 7/3). Thus, a yellow solid was obtained (208 mg, 77%).

後処理

  1. additionwere added
  2. temperatureAfter cooling it to room temperature
  3. washwashed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration, and concentration
  6. customThen, the residue obtained by concentration under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=97/3 to 7/3)
  8. customThus, a yellow solid was obtained (208 mg, 77%)

出典と根拠

ORDレコード
ord-fb17bd2a5fb640e9b9ec8cb20bfeb4f5
出典データセット
uspto-grants-2014_09
特許番号
US08829199B2

関連ノート

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