Potassium Carbonate → Methyl 2-(5-chloro-2-methyl-1H-indol-1-yl)acetate

HRID 1944444ノート

反応式

HRID 1944444 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]([CH3:15])=[CH:5]2.[C:16](=O)([O-])[O-].[K+].[K+].BrCC(OC)=O>CN(C)C=O>[CH3:16][O:13][C:12](=[O:14])[CH2:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[CH3:15]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 60074833(5-Chloro-2-methylindol-1-yl)acetic acid

生成物 1

HCID 60074868Methyl 2-(5-chloro-2-methyl-1H-indol-1-yl)acetate収率 101.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of (5-chloro-2-methylindol-1-yl)acetic acid (25 g), potassium carbonate (100 g) and N,N-dimethylformamide (220 mL) was treated dropwise with methyl bromoacetate (37 g), and the resulting mixture was stirred at 60° C. for 2 days. The mixture was cooled to room temperature and partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic solution was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and pentane (1:10 to 1:0 by volume) to afford the title compound as a white solid (27 g).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic solution was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with a mixture of dichloromethane and pentane (1:10 to 1:0 by volume)

出典と根拠

ORDレコード
ord-c032083b613143e79790eac64e61c3d4
出典データセット
uspto-grants-2013_03
特許番号
US08394836B2

反応ノート

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