Methyl iodide → ethyl 7-(methyl{[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate

HRID 504734

反応式

HRID 504734 の反応式
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18]2)(=[O:11])=[O:10].[C:29](=O)([O-])[O-].[K+].[K+].CI.CCCCCC>CN(C)C=O.C(OCC)(=O)C>[CH3:29][N:12]([S:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:27])([F:1])[F:28])(=[O:11])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18]2

参加物

7

反応物 4

HCID 6328Methyl iodide2 回HCID 8058HexaneHCID 11430Potassium CarbonateHCID 57476178ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate

生成物 1

HCID 59135580ethyl 7-(methyl{[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate収率 72%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate (5.0 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (50 mL) was added methyl iodide (0.75 mL) under ice-cooling, and the mixture was stirred from under ice-cooling to room temperature for 18 hr. The reaction solution was ice-cooled, methyl iodide (0.75 mL) was added again, and the mixture was stirred from under ice-cooling to room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed with water, aqueous citric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to basic silica gel column chromatography (ethyl acetate:hexane=20:80-35:65), and the obtained crude product was subjected three times to silica gel column chromatography (ethyl acetate:hexane=5:95-10:90) to give the title compound (3.7 g, yield: 72%) as a pale-yellow oil. MS: 427 (MH+).

後処理

  1. temperaturecooling
  2. temperaturecooled
  3. stirringthe mixture was stirred from under ice-
  4. temperaturecooling to room temperature for 18 hr
  5. washwashed with water, aqueous citric acid solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained crude product

出典と根拠

ORDレコード
ord-1b2689df54544c038f160d6ab2290f11
出典データセット
uspto-grants-2010_08
特許番号
US07777047B2

関連ノート

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