Water → Ethyl 5-(2-methoxyethoxy)-7-{methyl[(1-methyl-1H-imidazol-2-yl)sulfonyl]amino}-1H-indole-2-carboxylate

HRID 1960416ノート

反応式

HRID 1960416 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([NH:15][S:16]([C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)(=[O:18])=[O:17])[CH:14]=1)[NH:11][C:10]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:9]2.[C:30](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N:15]([CH3:30])[S:16]([C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)(=[O:17])=[O:18])[CH:14]=1)[NH:11][C:10]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:9]2

参加物

8

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59136127ethyl 5-(2-methoxyethoxy)-7-{[(1-methyl-1H-imidazol-2-yl)sulfonyl]amino}-1H-indole-2-carboxylate

生成物 1

HCID 59135907Ethyl 5-(2-methoxyethoxy)-7-{methyl[(1-methyl-1H-imidazol-2-yl)sulfonyl]amino}-1H-indole-2-carboxylate収率 92%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Ethyl 5-(2-methoxyethoxy)-7-{[(1-methyl-1H-imidazol-2-yl)sulfonyl]amino}-1H-indole-2-carboxylate (780 mg) was dissolved in N,N-dimethylformamide (10 mL), potassium carbonate (256 mg) and methyl iodide (0.15 mL) were added, and the mixture was stirred at room, temperature for 15.5 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=10:90-40:60) to give the title compound (740 mg, yield 92%) as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained crude product

出典と根拠

ORDレコード
ord-4d7c5be44ff24b239e7e80d0c2d35155
出典データセット
uspto-grants-2013_04
特許番号
US08410087B2

反応ノート

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